Access to CF3-Containing Cyclopentaquinolinone Derivatives from Indolyl-ynones via Silver-Catalyzed One-pot Reaction

Guifang Han,+a Li Xue,+a Lili Zhao,a Tiaozhen Zhu,a Jingli Hou,a
Yuguang Song,a,* and Yangping Liua,* a Tianjin Key Laboratory on Technologies Enabling Development of Clinical Therapeutics and Diagnostics, School of
Pharmacy, Tianjin Medical University, Tianjin 300070, People’s Republic of China
E-mail: songyuguang@tmu.edu.cn; liuyangping@tmu.edu.cn

These two authors contributed equally to this work.
Manuscript received: November 2, 2018; Revised manuscript received: November 30, 2018;
Version of record online: December 20, 2018
Supporting information for this article is available on the WWW under https://doi.org/10.1002/adsc.201801482

 

 

The trifluoromethyl (CF3) group is a privileged moiety in pharmaceuticals, agrochemicals and functional materials due to unique properties of trifluoromethylated molecules (e. g., elevated electronegativity, hydrophobicity, metabolic stability and bioavailability).[1] Much effort has been made to develop efficient methods for selective incorporation of the CF3 group into diverse skeletal structures.[2] Among them, transition metal-mediated or -catalyzed trifluoromethylation has accepted most attention, as they enable facile formation of both CC/C-heteroatom and CCF3 bonds in a single step.[3]

 

Carbotrifluoromethylation of alkenes or alkynes promoted by transition metals is a powerful strategy for the synthesis of complicated trifluoromethylated heterocyclic scaffolds with enhanced or distinct biological activities (Scheme 1).[4] For example, Liu,[4a] Sodeoka,[4b] Zhu[4c] and Nevado[4d] reported the synthesis of CF3-substituted oxindoles through intramolecular carbotrifluoromethylation, while Fu,[4e] Xiao[4f] and Ding[4g] utilized the endo-type carbotrifluoromethylation reaction to synthesize CF3-substituted dihydronaphthalenes, chromenes and coumarins. In addition, Wang[4h] and Liang[4i] independently reported copper-catalyzed trifluoromethylation of activated alkenes and alkynes to give spiroskelecton compounds. Zhu also reported the synthesis of trifluoromethylated naphthoquinones by copper-catalyzed cascade trifluoromethylation/cyclization of 2-(3-arylpropioloyl)benzaldehydes.[4j] Additionally, Liu developed a novel approach for the synthesis of benzannulated medium- and macro-ring scaffolds through 1,4(5)-aryl migration/ring expansion triggered by addition of the trifluoromethyl radicals to alkenes.[4k–m]

 

The spiroindolenine derivatives are an important class of biologically active molecules.[5] The trifluoromethylation/dearomatization reaction of indole represents a practical strategy to synthesize such CF3-
containing scaffolds. For example, Wang group reported a copper-catalyzed cascade reaction involving trifluoromethylation of acrylamides coupled with indole dearomatization.[4q] Recently, You developed a visible-light promoted trifluoromethylation of alkenes coupled with intramolecular indole dearomatization to afford CF3-substituted spiroindolenines.[4r] As part of our effort to synthesize trifluoromethylated heterocyclic compounds,[4h,q,6] we initially attempted to synthesize the spiro[cyclopentane-1,3’-indole] compound 2 a by trifluoromethylation of the indolyl-ynone
1 a, [7] followed by intramolecular indole dearomatization. Unexpectedly, the trifluoromethylated cyclopenta[c]quinolin-3-one 3 a was obtained. The cyclopentaquinolinone skeleton has been recognized as valuable scaffolds in natural products and synthetic pharmaceuticals.[8]

 

To efficiently obtain these cyclopentaquinolinone derivatives, the reaction conditions were optimized using the indolyl-ynone 1 a as a model substrate. The reaction was firstly carried out in the presence of
20 mol% of CuI as catalyst, 2 equivalents of 1-trifluoromethyl-1,2-benziodoxol-3-(1H)-one (Togni’s reagent)[9] as CF3 source at 80 8C under argon atmosphere in acetonitrile. 19F NMR results showed
that complicated products were generated in this reaction and the product 2 a was not detectable (Table 1). However, the CF3-containing quinoline 3 a was isolated from the reaction mixture in 21% yield
(Entry 1). The structure of 3 a was unambiguously determined by X-ray crystallography.[10] Encouraged by this novel result, we then investigated the effect of various catalysts on the reaction. The catalysts CuBr and CuCl proved to be ineffective (Entries 2 and 3).

 

To our delight, AgNO3 was more effective, leading to the desired product 3 a in a moderate yield (64%, isolated yield) (Entry 4). Other silver catalysts including Ag2O, Ag2CO3, AgOTf and AgOAc were also
tested (Entries 5–8) but the results were not improved.

 

Subsequently, the solvent effect was also explored using 1,2-dichloroethane (DCE), DMSO, THF and DMF. However, the yields were not improved as comparison to CH3CN (Entries 9–12). Interestingly,
the reaction in the absence of the Togni’s reagent resulted in the product 2 b in quantitative yield (Entry 13).[7] Considering that the spiro-indolenine 2 b may be the reaction intermediate, its reaction with the Togni’s reagent was carried out under the same condition and a single product 3 a was obtained in 95% yield (Entry 14). Based on the above results, the sequential one-pot reaction was used to synthesize the product 3 a in which the indolyl-ynone 1 a was stirred with AgNO3 for 3 h at room temperature, followed by addition of Togni’s reagent. Gratifyingly, the compound 3 a was obtained in high yield (92%, Entry 15).

With the optimized reaction conditions in hand (Table 1, Entry 15), we next explored the substrate scope of the reaction (Table 2). First, we checked the effect from the substituent on the alkyne-linked aryl
ring (R1). It was found that the substrates with the electron-donating groups such as OMe and Me at the meta or para position of the phenyl ring (1 b–d) afforded the products 3 b–d in good to excellent yields (79–85% yields). Of note is that the introduction of N, N-dimethylamino group at the para position has a detrimental effect on the reaction, leading only to trace amount of the product 3 e. This is possibly due to the strong propensity of the dimethylaminobenzene group to form the corresponding radical cation on the nitrogen atom, resulting in uncontrollable side reactions.[11] On the other hand, this reaction was also suitable for the substrates with electron-withdrawing groups on the phenyl ring, affording the corresponding quinoline products (3 f–3i) in moderate to excellent yields. Specifically, the substrates with F, Cl and Br groups on the phenyl ring afforded the products 3 f, 3 g and 3 h in 90%, 89% and 83% yields. The replacement of the phenyl ring with thiophenyl group also led to
the corresponding products 3 k in 45% yield. Unfortunately, the substrates with alkyl groups (e. g., cyclohexyl and butyl) afforded complex mixtures (3l and 3m) that were hard to be purified.

 

Furthermore, we studied the effect from the substitutents on the indole ring (R2). Results showed that the reaction was insensitive to the electronic effects of R2. The substrates with either electrondonating groups (5-Me and 5-OMe) or electron-withdrawing groups (5-F, 5-Cl, and 5-Br) afforded the desired products (3 n–3 u) in moderate to good yields. It was noteworthy that the substrates with 4-Me or 2-Ph groups on the indole ring provided the products 3 o and 3 v in relatively low yields of 38% and 32%, respectively. The substrate with 2-Me failed to yield the desired product 3 w (<5%). These low yields are
possibly associated with the steric repulsion of the neighboring groups to 4-Me, 2-Ph and 2-Me.

 

To provide a reasonable mechanism for the silvercatalyzed cascade reaction, control experiments were also carried out. The silver-catalyzed reaction of 2 b with the Togni’s reagent was conducted in the presence of radical scavengers TEMPO or 2,6-di-tbutyl-4-methylphenol (BHT) (Scheme 2). Results showed that the yield was inversely related to the concentration of the scavengers with strong inhibition
to the reaction in the presence of 200 mol% of TEMPO (trace) and BHT (19%). In the case of TEMPO, the corresponding TEMPO-CF3 adduct was detected by 19F NMR, indicating that a radical species
is involved in this process possibly via a single-electron transfer (SET) mechanism. This result was further confirmed by the formation of TEMPO-CF3 from silver-catalyzed reaction of TEMPO with the Togni’s reagent, accompanied with the attenuation of EPR signal intensity of TEMPO (see SI).

 

According to our present results and previously reported results in the literatures,[4,6] the reaction mechanism is proposed (Scheme 3). Firstly, the triple bond of the ynone 1 a is activated by Ag(I) as p-acidic
catalyst and the spirocyclic indolenine intermediate 2 b is formed through dearomatizing spirocyclization.[7c,d] Secondly, Ag(I) as Lewis acid catalyst promotes the enolate I formation and subsequent
cyclopropanation to form II, which is further transformed into III. Then, the CF3 radical which is formed from the Togni’s reagent upon activation by Ag(I) attacks the reactive intermediate III to result in IV
and Ag(0). And Ag(0) is oxidized possibly by Ag(II) or Togni’s reagent back to Ag(I) for the next reaction cycle. Finally, the intermediate IV is oxidized possibly by Togni’s reagent[12] or Ag(II) to give CF3-containing quinoline 3 a. It was reported in a previous study that the spiro-indolenine 2 b may be transformed into the quinoline 4 a upon catalysis by acid.[7b,c] However, this mechanism may not exist in the present reaction since the product 3 a was produced in very low yield (~20%) from the reaction of the quinoline 4 a with the Togni’s reagent (Scheme 2).

In summary, we herein report an Ag(I)-catalyzed cascade reaction of the substituted indolyl-ynones with the Togni reagent, which includes indole dearomatization, ring expansion, trifluoromethylation and
dehydrogenation. This reaction allows regiospecific and efficient construction of a wide range of trifluoromethylated cyclopenta[c]quinolin-3-ones, which are valuable scaffolds and have great potential in medicinal chemistry. Moreover, this new mechanism provides new opportunity for the synthesis of other trifluoromethylated heterocyclic and polycyclic scaffolds.

 

Experimental Section
General procedure for the synthesis of 3 a–w. To an oven dried Schlenk tube precharged with indol-ynone 1 (0.2 mmol, 1.0 equiv.) in CH3CN (3 mL) was added AgNO3 (6.8 mg, 20 mol%). The mixture was stirred at RT until the compound 1 was completely consumed as detected by TLC. The Schlenk tube was carefully evacuated and refilled with nitrogen (this process was repeated three times). Then,
Togni’s reagent II (126.4 mg, 0.4 mmol, 2.0 equiv.) was added. The resulting reaction mixture was stirred at 988C for 24 h and quenched by saturated aqueous solution of NaHCO3 (20 mL). The organic layer was separated and the aqueous layer was extracted with EA (20 mL*3). The combined organic layer was washed with saturated aqueous solution of NaHCO3 and saturated brine, and concentrated
under in vacuo. The resulting residue was purified by flash column chromatography (elution: PE:EA=20:1–5:1) to give the desired compound 3.

 

Acknowledgements
This work was financially supported by the National Natural Science Foundation of China (No. 21871210, 21603163, 21572161, 31500684 and 81603064), the Science & Technology Projects of Tianjin (No. 15JCZDJC32300 and 15JCYBJC23700) and Tianjin Municipal 13th five-year plan (Tianjin Medical University Talent Project).

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CAS No. 102053-79-2 2-Propenoic acid, 3-(2-acetyl-3-thienyl)-, methyl ester, (E)- (9CI) Catalog No.:AG0006H2 MDL No.: MF:C10H10O3S MW:210.2496	CAS No. 102054-10-4 2-Butenedioic acid (2Z)-, 1,4-bis(2-methoxy-1-methylethyl) ester Catalog No.:AG0006H1 MDL No.: MF: MW:	CAS No. 102054-53-5 Phosphorodiamidic chloride, N,N'-bis(2-oxo-3-oxazolidinyl)- Catalog No.:AG0006H0 MDL No.: MF:C6H10ClN4O5P MW:284.5942
CAS No. 102055-59-4 Rhenium hydroxide Catalog No.:AG0006GZ MDL No.: MF:H4O4Re MW:254.2364	CAS No. 102056-64-4 1,3-Cyclopentadiene, [3-(ethoxysilyl)propyl]- Catalog No.:AG0006GY MDL No.: MF:C10H18OSi MW:182.3348	CAS No. 102056-77-9 Butane, methyl- (9CI) Catalog No.:AG0006GX MDL No.: MF:C5H12 MW:72.1488
CAS No. 102056-97-3 L-Homoserine, N-(triphenylmethyl)-, compd. with N,N-diethylethanamine (1:1) Catalog No.:AG0006GW MDL No.: MF:C29H38N2O3 MW:462.6236	CAS No. 1020568-10-8 2,4-Quinolinedicarboxylic acid, 7-bromo-, 2,4-dimethyl ester Catalog No.:AG0006GP MDL No.:MFCD11976156 MF:C13H10BrNO4 MW:324.1268	CAS No. 1020569-65-6 4-Isoxazolecarboxylic acid, 5-cyclopropyl-3-(2,6-dichlorophenyl)-, ethyl ester Catalog No.:AG0006GO MDL No.:MFCD16652286 MF:C15H13Cl2NO3 MW:326.1746
CAS No. 1020571-45-2 1-Pyrrolidinecarboxylic acid, 3,4-diamino-, 1,1-dimethylethyl ester, (3S,4S)- Catalog No.:AG0006GN MDL No.:MFCD14635703 MF:C9H19N3O2 MW:201.2661	CAS No. 1020572-61-5 2-Quinolinecarboxylic acid, 6-bromo-, ethyl ester Catalog No.:AG0006GM MDL No.: MF:C12H10BrNO2 MW:280.1173	CAS No. 1020574-89-3 2-Quinolinecarboxylic acid, 6-bromo-7-fluoro-, ethyl ester Catalog No.:AG0006GL MDL No.: MF:C12H9BrFNO2 MW:298.1078
CAS No. 1020575-89-6 Benzenemethanol, 5-bromo-α-methyl-2-nitro- Catalog No.:AG0006GK MDL No.:MFCD10698996 MF:C8H8BrNO3 MW:246.0580	CAS No. 1020576-70-8 1-Isoquinolinecarboxylic acid, 6-bromo-, ethyl ester Catalog No.:AG0006GJ MDL No.:MFCD18257309 MF:C12H10BrNO2 MW:280.1173	CAS No. 102058-65-1 2(3H)-Naphthalenone, 4,4a,5,6,7,8-hexahydro-5-hydroxy-1,4a-dimethyl- Catalog No.:AG0006GV MDL No.: MF:C12H18O2 MW:194.2701
CAS No. 102058-98-0 Benzene, 1,1'-[[1,2-bis(methylene)-1,2-ethanediyl]bis(thio)]bis- Catalog No.:AG0006GU MDL No.: MF:C16H14S2 MW:270.4124	CAS No. 102059-18-7 Acetamide, N-[4-[(1E)-3-oxo-3-phenyl-1-propen-1-yl]phenyl]- Catalog No.:AG0006GT MDL No.: MF:C17H15NO2 MW:265.3065	CAS No. 102059-22-3 1,2,5,8-Dithiadiazecine, octahydro-3,3,6,6,10,10-hexamethyl- Catalog No.:AG0006GS MDL No.: MF:C12H26N2S2 MW:262.4782
CAS No. 102059-70-1 1,3-Benzenedicarboxylic acid, 5-(benzoyloxy)- Catalog No.:AG0006GR MDL No.: MF:C15H10O6 MW:286.2363	CAS No. 102059-84-7 Cerium, compd. with niobium (1:1) Catalog No.:AG0006GQ MDL No.: MF:CeNb MW:233.0224	CAS No. 10206-02-7 1H-Naphth[2,3-d]imidazole, 2-(2-pyridinyl)- Catalog No.:AG0006HU MDL No.: MF:C16H11N3 MW:245.2786
CAS No. 10206-04-9 phenanthro[9,10-d]oxazole, 2-(4-chlorophenyl)- Catalog No.:AG0006HT MDL No.: MF:C21H12ClNO MW:329.7791	CAS No. 102061-91-6 5-Pyrimidinecarboxylic acid, 1,6-dihydro-2-(methylthio)-6-oxo-, ethyl ester, sodium salt (1:1) Catalog No.:AG0006HS MDL No.: MF:C8H10N2NaO3S MW:237.2314	CAS No. 102062-36-2 1-Propanesulfonic acid, 3-[(4'-amino-3,3',5,5'-tetramethyl[1,1'-biphenyl]-4-yl)amino]- Catalog No.:AG0006HR MDL No.: MF:C19H26N2O3S MW:362.4863
CAS No. 102062-46-4 1-Propanesulfonic acid, 3-[(4'-amino-3,3',5,5'-tetramethyl[1,1'-biphenyl]-4-yl)amino]-, sodium salt (1:1) Catalog No.:AG0006HQ MDL No.:MFCD00077876 MF:C19H25N2NaO3S MW:384.4682	CAS No. 102063-87-6 Urea, N'-(2-aminoethyl)-N-methyl-N-phenyl- Catalog No.:AG0006HP MDL No.: MF:C10H15N3O MW:193.2456	CAS No. 1020635-54-4 3-Pyridinecarboxylic acid, 2-methoxy-5-nitro- Catalog No.:AG0006HB MDL No.:MFCD11052413 MF:C7H6N2O5 MW:198.1329
CAS No. 102064-36-8 Pyrido[3,2-e]pyrrolo[1,2-a]pyrazin-6(5H)-one Catalog No.:AG0006HO MDL No.: MF:C10H7N3O MW:185.1821	CAS No. 102064-43-7 Pyrazolo[1,5-a]pyridine, 3-bromo-2-(1-methylethyl)- Catalog No.:AG0006HN MDL No.: MF:C10H11BrN2 MW:239.1117	CAS No. 102065-48-5 1H-1,2,4-Triazole, 1-(triethylstannyl)- Catalog No.:AG0006HM MDL No.: MF:C8H17N3Sn MW:273.9417
CAS No. 102065-86-1 3-Azetidinamine Catalog No.:AG0006HL MDL No.:MFCD06858460 MF:C3H8N2 MW:72.1090	CAS No. 102065-87-2 Acetamide, N-[1-(diphenylmethyl)-3-azetidinyl]- Catalog No.:AG0006HK MDL No.: MF:C18H20N2O MW:280.3642	CAS No. 102065-89-4 3-Azetidinamine, hydrochloride (1:2) Catalog No.:AG0006HJ MDL No.:MFCD09910173 MF:C3H10Cl2N2 MW:145.0309
CAS No. 102065-92-9 Acetamide, N-3-azetidinyl-, hydrochloride (1:1) Catalog No.:AG0006HI MDL No.:MFCD08059477 MF:C5H11ClN2O MW:150.6066	CAS No. 102065-94-1 2H-1,4-Benzoxazin-3(4H)-one, 8-methyl- Catalog No.:AG0006HH MDL No.:MFCD09835009 MF:C9H9NO2 MW:163.1733	CAS No. 102066-01-3 Acetamide, 2-(2-bromo-4-methylphenoxy)- Catalog No.:AG0006HG MDL No.:MFCD02012260 MF:C9H10BrNO2 MW:244.0852
CAS No. 1020665-66-0 Cyclohexanamine, 2-isothiocyanato-N,N-dimethyl-, (1R,2R)- Catalog No.:AG0006HA MDL No.: MF:C9H16N2S MW:184.3017	CAS No. 1020665-67-1 Benzenesulfonamide, N-[(1R,2R)-2-amino-1,2-diphenylethyl]-3,5-bis(trifluoromethyl)- Catalog No.:AG0006H9 MDL No.: MF:C22H18F6N2O2S MW:488.4459	CAS No. 1020665-73-9 Benzenesulfonamide, N-[(1R,2R)-2-[[[[(1R,2R)-2-(dimethylamino)cyclohexyl]amino]thioxomethyl]amino]-1,2-diphenylethyl]-3,5-bis(trifluoromethyl)- Catalog No.:AG0006H8 MDL No.: MF:C31H34F6N4O2S2 MW:672.7477
CAS No. 102067-51-6 Furan, 3-chloro-2-ethyltetrahydro-, (2R,3R)-rel- Catalog No.:AG0006HF MDL No.: MF:C6H11ClO MW:134.6039	CAS No. 102069-16-9 Phosphonic acid, [3-[[3-[1,2-bis(oxiranylmethyl)-3,5-dioxo-1,2,4-triazolidin-4-yl]-2-hydroxypropyl]amino]-1-hydroxypropylidene]bis- (9CI) Catalog No.:AG0006HE MDL No.: MF:C14H26N4O12P2 MW:504.3234	CAS No. 102069-17-0 Acetic acid, 2-cyano-, 2-(2-methylpropoxy)-2-oxoethyl ester Catalog No.:AG0006HD MDL No.: MF:C9H13NO4 MW:199.2038
CAS No. 102069-18-1 Acetic acid, 2-cyano-, 2-(3-methylbutoxy)-2-oxoethyl ester Catalog No.:AG0006HC MDL No.: MF:C10H15NO4 MW:213.2304	CAS No. 102069-58-9 1,4,7-Trioxa-10-azacyclododecane, 10-dodecyl- Catalog No.:AG0006II MDL No.: MF:C20H41NO3 MW:343.5444	CAS No. 102069-72-7 1H-Imidazolium, 1-decyl-3-[(hexylthio)methyl]-, chloride (1:1) Catalog No.:AG0006IH MDL No.: MF:C20H41ClN2S MW:377.0709
CAS No. 102069-83-0 Methanone, [(2S)-2-(hydroxymethyl)-1-pyrrolidinyl](2-methoxyphenyl)- Catalog No.:AG0006IG MDL No.: MF:C13H17NO3 MW:235.2790	CAS No. 102069-84-1 Methanone, [(2S)-2-(methoxymethyl)-1-pyrrolidinyl](2-methoxyphenyl)- Catalog No.:AG0006IF MDL No.: MF:C14H19NO3 MW:249.3056	CAS No. 102069-85-2 Methanone, [(2S)-2-[(methoxymethoxy)methyl]-1-pyrrolidinyl](2-methoxyphenyl)- Catalog No.:AG0006IE MDL No.: MF:C15H21NO4 MW:279.3315
CAS No. 102069-99-8 Benzene, [(1-ethoxyethenyl)oxy]- Catalog No.:AG0006ID MDL No.: MF:C10H12O2 MW:164.2011	CAS No. 10207-75-7 7-Octene-1,6-diol, 2,6-dimethyl- Catalog No.:AG0006IJ MDL No.: MF:C10H20O2 MW:172.2646	CAS No. 102070-04-2 4-Nonyn-3-ol, 2,2-diethoxy- Catalog No.:AG0006IC MDL No.: MF:C13H24O3 MW:228.3279
CAS No. 102070-37-1 Benzene, 1,1',1''-[2-propen-1-yl-3-ylidenetris(thio)]tris- (9CI) Catalog No.:AG0006IB MDL No.: MF:C21H18S3 MW:366.5626	CAS No. 102070-99-5 4-Piperidinecarboxylic acid, 1-methyl-4-[[(phenylthio)carbonyl]oxy]-, methyl ester Catalog No.:AG0006IA MDL No.: MF:C15H19NO4S MW:309.3807	CAS No. 102071-16-9 2,6-Piperidinediethanol, 1-methyl-α2,α2,α6-triphenyl-, hydrochloride (1:1) Catalog No.:AG0006I9 MDL No.: MF:C28H34ClNO2 MW:452.0281
CAS No. 102071-21-6 1H-Purine-2,6-dione, 8-bromo-3,9-dihydro-1,3-dimethyl-, compd. with 4-(diphenylmethoxy)-1-methylpiperidine (1:1) Catalog No.:AG0006I8 MDL No.: MF:C26H30BrN5O3 MW:540.4521	CAS No. 102071-23-8 1H-Purine-2,6-dione, 8-chloro-3,9-dihydro-1,3-dimethyl-, compd. with 3-[(diphenylmethoxy)methyl]-1-methylpiperidine (1:1) Catalog No.:AG0006I7 MDL No.: MF:C27H32ClN5O3 MW:510.0277	CAS No. 102071-71-6 2-Benzothiazoleethanol, α,α-bis(trifluoromethyl)- Catalog No.:AG0006I6 MDL No.: MF:C11H7F6NOS MW:315.2348
CAS No. 102071-74-9 Benzenepropanol, α,α-bis(chlorodifluoromethyl)- Catalog No.:AG0006I5 MDL No.: MF:C11H10Cl2F4O MW:305.0961	CAS No. 102071-75-0 1-Piperidinepropanol, β,β-bis(1-piperidinylmethyl)- Catalog No.:AG0006I4 MDL No.: MF:C20H39N3O MW:337.5432	CAS No. 102071-77-2 1,4-Benzodioxin-2-propanol, 6,7-dichloro-2,3-dihydro- Catalog No.:AG0006I3 MDL No.: MF:C11H12Cl2O3 MW:263.1172
CAS No. 102071-87-4 1-Propanone, 3-[[(2,3-dihydro-1,4-benzodioxin-2-yl)methyl]amino]-1-(2-methyl-1-piperidinyl)- Catalog No.:AG0006I2 MDL No.: MF:C18H26N2O3 MW:318.4106	CAS No. 102071-88-5 1-Propanone, 3-[[(2,3-dihydro-1,4-benzodioxin-2-yl)methyl]amino]-1-(4-morpholinyl)- Catalog No.:AG0006I1 MDL No.: MF:C16H22N2O4 MW:306.3569	CAS No. 102071-89-6 1-Propanone, 3-[[(2,3-dihydro-1,4-benzodioxin-2-yl)methyl]amino]-1-(1-piperidinyl)- Catalog No.:AG0006I0 MDL No.: MF:C17H24N2O3 MW:304.3841
CAS No. 102071-90-9 1-Propanone, 3-[[(2,3-dihydro-1,4-benzodioxin-2-yl)methyl]amino]-1-(1-pyrrolidinyl)- Catalog No.:AG0006HZ MDL No.: MF:C16H22N2O3 MW:290.3575	CAS No. 1020714-78-6 Propanoic acid, 3-azido-2-(benzoyloxy)- Catalog No.:AG0006HY MDL No.: MF:C10H9N3O4 MW:235.1962	CAS No. 1020717-98-9 Pyridine, 4-bromo-2,3-dichloro- Catalog No.:AG0006HX MDL No.:MFCD09743493 MF:C5H2BrCl2N MW:226.8861
CAS No. 1020717-99-0 Benzoic acid, 4-bromo-5-fluoro-2-nitro- Catalog No.:AG0006HW MDL No.:MFCD08702773 MF:C7H3BrFNO4 MW:264.0054	CAS No. 1020718-00-6 Benzene, 1-(chloromethyl)-2-fluoro-3-nitro- Catalog No.:AG0006HV MDL No.:MFCD09955448 MF:C7H5ClFNO2 MW:189.5715	CAS No. 1020718-01-7 Benzene, 2-bromo-3,4,5-trifluoro-1-nitro- Catalog No.:AG0006J8 MDL No.:MFCD09955450 MF:C6HBrF3NO2 MW:255.9768
CAS No. 1020718-20-0 Benzoyl chloride, 2-bromo-6-fluoro- Catalog No.:AG0006J7 MDL No.:MFCD09038470 MF:C7H3BrClFO MW:237.4535	CAS No. 1020718-25-5 2,4,6,8,10,12-Docosahexaenoic acid, ethyl ester Catalog No.:AG0006J6 MDL No.: MF:C24H36O2 MW:356.5414	CAS No. 1020718-50-6 2-Pyrrolidinone, 4-(2-methoxyphenyl)- Catalog No.:AG0006J5 MDL No.: MF:C11H13NO2 MW:191.2264
CAS No. 1020718-53-9 Carbamic acid, N-[5-(4-fluorophenyl)-5-oxopentyl]-, 1,1-dimethylethyl ester Catalog No.:AG0006J4 MDL No.:MFCD09955053 MF:C16H22FNO3 MW:295.3492	CAS No. 1020718-59-5 Benzoic acid, 4-(6-chloro-2-pyrazinyl)-, methyl ester Catalog No.:AG0006J3 MDL No.:MFCD09753806 MF:C12H9ClN2O2 MW:248.6651	CAS No. 1020718-62-0 Benzoic acid, 4-(6-bromo-2-pyridinyl)-2-methyl- Catalog No.:AG0006J2 MDL No.: MF:C13H10BrNO2 MW:292.1280
CAS No. 1020718-65-3 Benzoic acid, 3-(6-bromo-2-pyridinyl)-4-methyl-, methyl ester Catalog No.:AG0006J1 MDL No.: MF:C14H12BrNO2 MW:306.1546	CAS No. 1020718-68-6 Benzoic acid, 4-(6-bromo-2-pyridinyl)-3-methyl- Catalog No.:AG0006J0 MDL No.: MF:C13H10BrNO2 MW:292.1280	CAS No. 1020718-69-7 Benzaldehyde-2,3,4,5-d4, 6-nitro- Catalog No.:AG0006IZ MDL No.: MF:C7HD4NO3 MW:155.1441
CAS No. 1020718-71-1 Benzoic acid, 4-(6-chloro-2-pyrazinyl)-3-methyl- Catalog No.:AG0006IY MDL No.: MF:C12H9ClN2O2 MW:248.6651	CAS No. 1020718-72-2 Benzaldehyde-2,3,5,6-d4, 4-nitro- Catalog No.:AG0006IX MDL No.:MFCD04039637 MF:C7HD4NO3 MW:155.1441	CAS No. 1020718-74-4 Benzoic acid, 4-(6-chloro-2-pyrazinyl)-2-methyl- Catalog No.:AG0006IW MDL No.: MF:C12H9ClN2O2 MW:248.6651
CAS No. 1020718-75-5 Benzene-2,3,5,6-d4-sulfonic acid-d, 4-(acetylamino-d)- Catalog No.:AG0006IV MDL No.: MF:C8H3D6NO4S MW:221.2633	CAS No. 1020718-78-8 Acetamide-2,2,2-d3, N-[4-(sulfooxy)phenyl]- Catalog No.:AG0006IU MDL No.: MF:C8H6D3NO5S MW:234.2442	CAS No. 1020718-81-3 1,3-Propanediol, 2-[2-(2-amino-6-chloro-9H-purin-9-yl)ethyl-1,1,2,2-d4]-, 1,3-diacetate Catalog No.:AG0006IT MDL No.: MF:C14H14ClD4N5O4 MW:359.8015
CAS No. 1020718-84-6 Benzene-2,3,5,6-d4-sulfonyl chloride, 4-(acetylamino-d)- Catalog No.:AG0006IS MDL No.: MF:C8H3ClD5NO3S MW:238.7028	CAS No. 1020718-91-5 Acetamide, N-[4-[(2-thiazolylamino)sulfonyl]phenyl-2,3,5,6-d4]- Catalog No.:AG0006IR MDL No.: MF:C11H7D4N3O3S2 MW:301.3780	CAS No. 1020718-93-7 [1,1'-Biphenyl-2,2',3',4,4',5,5',6,6'-d9]-3-amine Catalog No.:AG0006IQ MDL No.: MF: MW:
CAS No. 1020718-95-9 5,6-Quinolinediamine, N6-(methyl-d3)- Catalog No.:AG0006IP MDL No.: MF:C10H8D3N3 MW:176.2329	CAS No. 1020718-97-1 [1,1'-Biphenyl-2',3',4',5',6'-d5]-4-amine, 3-methyl- Catalog No.:AG0006IO MDL No.: MF: MW:	CAS No. 1020719-00-9 3-Pyridine-2,4,5,6-d4-methanamine Catalog No.:AG0006IN MDL No.: MF:C6H4D4N2 MW:112.1658
CAS No. 1020719-03-2 2,3-Pyridinediamine, N3-(methyl-d3)-5-phenyl- Catalog No.:AG0006IM MDL No.: MF:C12H10D3N3 MW:202.2702	CAS No. 1020719-05-4 2,3'-Bipyridine-2',4',5',6'-d4, 3,4,5,6-tetrahydro- Catalog No.:AG0006IL MDL No.: MF:C10H8D4N2 MW:164.2403	CAS No. 1020719-11-2 2,3'-Bipyridine-2',4',5',6'-d4, 1,2,3,6-tetrahydro- Catalog No.:AG0006IK MDL No.: MF:C10H8D4N2 MW:164.2403
CAS No. 1020719-18-9 Pentanamide, 4-methyl-3-oxo-N-[2-(phenylmethoxy)phenyl]-2-(phenyl-2,3,4,5,6-d5-methylene)- Catalog No.:AG0006JX MDL No.: MF:C26H20D5NO3 MW:404.5124	CAS No. 1020719-20-3 Pentanamide, 4-methyl-3-oxo-N-[4-(phenylmethoxy)phenyl]-2-(phenyl-2,3,4,5,6-d5-methylene)- Catalog No.:AG0006JW MDL No.: MF:C26H20D5NO3 MW:404.5124	CAS No. 1020719-21-4 3H-1,2,4-Triazol-3-one, 2,4-dihydro-4-[4-[4-(4-hydroxyphenyl)-1-piperazinyl]phenyl]-2-(1-methylpropyl-2,2,3,3,3-d5)- Catalog No.:AG0006JV MDL No.: MF:C22H22D5N5O2 MW:398.5129
CAS No. 1020719-22-5 3H-1,2,4-Triazol-3-one, 2,4-dihydro-4-[4-[4-(4-methoxyphenyl)-1-piperazinyl]phenyl]-2-(1-methylpropyl-2,2,3,3,3-d5)- Catalog No.:AG0006JU MDL No.: MF:C23H24D5N5O2 MW:412.5395	CAS No. 1020719-23-6 2-Butyne-1,1,4,4-d4-1,4-diol, 1,4-diacetate Catalog No.:AG0006JT MDL No.: MF:C8H6D4O4 MW:174.1872	CAS No. 1020719-24-7 3-Pyridinecarboxylic acid, 1,6-dihydro-6-oxo-1-(phenyl-2,3,4,5,6-d5)- Catalog No.:AG0006JS MDL No.: MF:C12H4D5NO3 MW:220.2356
CAS No. 1020719-25-8 2-Propanol, 1-(9H-carbazol-4-yloxy)-3-[[2-[2-(methoxy-d3)phenoxy]ethyl]amino]- Catalog No.:AG0006JR MDL No.: MF:C24H23D3N2O4 MW:409.4927	CAS No. 1020719-26-9 Benzene, 1-(2-chloroethoxy)-4-[1-[4-[[(1,1-dimethylethyl)dimethylsilyl]oxy]phenyl]-2-phenyl-1-buten-1-yl-3,3,4,4,4-d5]- Catalog No.:AG0006JQ MDL No.: MF:C30H32ClD5O2Si MW:498.1829	CAS No. 1020719-27-0 Phenol, 4-[1-[4-(2-chloroethoxy)phenyl]-2-phenyl-1-buten-1-yl-3,3,4,4,4-d5]- Catalog No.:AG0006JP MDL No.: MF:C24H18ClD5O2 MW:383.9220
CAS No. 1020719-30-5 1H-Imidazo[4,5-b]pyridine, 2-chloro-1-(methyl-d3)-6-phenyl- Catalog No.:AG0006JO MDL No.: MF:C13H7ClD3N3 MW:246.7101	CAS No. 1020719-31-6 Benzeneacetonitrile, α-(1-hydroxycyclohexyl-3,3,4,4,5,5-d6)-4-methoxy- Catalog No.:AG0006JN MDL No.: MF:C15H13D6NO2 MW:251.3538	CAS No. 1020719-32-7 3-Pyridine-2,4,5,6-d4-carbonitrile Catalog No.:AG0006JM MDL No.: MF:C6D4N2 MW:108.1340
CAS No. 1020719-39-4 5H-Dibenz[b,f]azepine-1,2,3,4-d4-5-carboxamide, 10,11-dihydro-10-hydroxy- Catalog No.:AG0006JL MDL No.: MF:C15H10D4N2O2 MW:258.3085	CAS No. 1020719-40-7 3-Pyridine-2,4,5,6-d4-methanamine, N-(diphenylmethylene)- Catalog No.:AG0006JK MDL No.: MF:C19H12D4N2 MW:276.3684	CAS No. 1020719-41-8 Propanoic acid, 3-(methyl-d3-thio)-, ethyl ester Catalog No.:AG0006JJ MDL No.: MF:C6H9D3O2S MW:151.2418
CAS No. 1020719-43-0 Benzenebutanamide, 4-fluoro-α-(2-methyl-1-oxopropyl)-γ-oxo-β-(phenyl-2,3,4,5,6-d5)-N-[2-(phenylmethoxy)phenyl]- Catalog No.:AG0006JI MDL No.: MF:C33H25D5FNO4 MW:528.6248	CAS No. 1020719-44-1 Benzenebutanamide, 4-fluoro-α-(2-methyl-1-oxopropyl)-γ-oxo-β-(phenyl-2,3,4,5,6-d5)-N-[4-(phenylmethoxy)phenyl]- Catalog No.:AG0006JH MDL No.: MF:C33H25D5FNO4 MW:528.6248	CAS No. 1020719-47-4 Acetamide-2,2,2-d3, N-(3,4-dihydroxyphenyl)- Catalog No.:AG0006JG MDL No.: MF:C8H6D3NO3 MW:170.1804
CAS No. 1020719-48-5 2H-Imidazo[4,5-b]pyridin-2-one, 1,3-dihydro-1-(methyl-d3)-6-phenyl- Catalog No.:AG0006JF MDL No.: MF:C13H8D3N3O MW:228.2644	CAS No. 1020719-49-6 Benzeneacetic acid, 4-(4-hydroxy-1-butyn-1-yl)-α,α-di(methyl-d3)-, methyl ester Catalog No.:AG0006JE MDL No.: MF:C15H12D6O3 MW:252.3386	CAS No. 1020719-50-9 Methanesulfonothioic acid, S-(2-hydroxyethyl-1,1,2,2-d4) ester Catalog No.:AG0006JD MDL No.: MF:C3H4D4O3S2 MW:160.2485
CAS No. 1020719-51-0 Benzoic acid, 3-hydroxy-2-(methyl-d3)- Catalog No.:AG0006JC MDL No.: MF:C8H5D3O3 MW:155.1658	CAS No. 1020719-52-1 2(1H)-Pyridinone, 5-(hydroxymethyl)-1-(phenyl-2,3,4,5,6-d5)- Catalog No.:AG0006JB MDL No.: MF:C12H6D5NO2 MW:206.2520	CAS No. 1020719-54-3 9H-Purine-9-ethan-α,β,β-d3-ol, 6-amino-α-(methyl-d3)- Catalog No.:AG0006JA MDL No.: MF:C8H5D6N5O MW:199.2428
CAS No. 1020719-55-4 4H-Pyrido[1,2-a]pyrimidin-4-one, 3-[2-[4-(6-fluoro-1,2-benzisoxazol-3-yl)-1-piperidinyl]ethyl-1,1,2,2-d4]-6,7,8,9-tetrahydro-9-hydroxy-2-methyl- Catalog No.:AG0006J9 MDL No.: MF:C23H23D4FN4O3 MW:430.5085	CAS No. 1020719-58-7 Benzeneacetic acid, α,α-di(methyl-d3)-4-[4-[(methylsulfonyl)oxy]-1-butyn-1-yl]-, methyl ester Catalog No.:AG0006KI MDL No.: MF:C16H14D6O5S MW:330.4290	CAS No. 1020719-60-1 Benzamide, 3-methoxy-2-(methyl-d3)-N-phenyl- Catalog No.:AG0006KH MDL No.: MF:C15H12D3NO2 MW:244.3036
CAS No. 1020719-61-2 3-Pyridinemethanol, α-[3-(methyl-d3-nitrosoamino)propyl]- Catalog No.:AG0006KG MDL No.: MF:C10H12D3N3O2 MW:212.2635	CAS No. 1020719-62-3 2(1H)-Pyridinone, 5-methyl-1-(phenyl-2,3,4,5,6-d5)- Catalog No.:AG0006KF MDL No.: MF:C12H6D5NO MW:190.2526	CAS No. 1020719-63-4 Propanethioamide-3,3,3-d3, 2-(methyl-d3)- Catalog No.:AG0006KE MDL No.: MF:C4H3D6NS MW:109.2229
CAS No. 1020719-64-5 Propanamide-3,3,3-d3, 2-(methyl-d3)- Catalog No.:AG0006KD MDL No.: MF:C4H3D6NO MW:93.1573	CAS No. 1020719-68-9 Pyridine-2,3,4,6-d4, 5-(1-nitroso-2-piperidinyl)- Catalog No.:AG0006KC MDL No.: MF:C10H9D4N3O MW:195.2544	CAS No. 1020719-69-0 2,3'-Bipyridine-2',4',5',6'-d4, 1,2,3,6-tetrahydro-1-nitroso- Catalog No.:AG0006KB MDL No.: MF:C10H7D4N3O MW:193.2385
CAS No. 1020719-72-5 6H-Purin-6-one, 2-amino-1,9-dihydro-9-[4-hydroxy-3-(hydroxymethyl)butyl-3,3,4,4-d4]- Catalog No.:AG0006KA MDL No.: MF: MW:	CAS No. 1020719-76-9 4H-Pyrido[1,2-a]pyrimidin-4-one, 3-[2-[4-(6-fluoro-1,2-benzisoxazol-3-yl)-1-piperidinyl]ethyl-1,1,2,2-d4]-6,7,8,9-tetrahydro-2-methyl- Catalog No.:AG0006K9 MDL No.: MF:C23H23D4FN4O2 MW:414.5091	CAS No. 1020719-78-1 Benzene-2,3,5,6-d4-sulfonamide, 4-amino-N-2-pyrimidinyl- Catalog No.:AG0006K8 MDL No.: MF:C10H6D4N4O2S MW:254.3016
CAS No. 1020719-96-3 1H-Isoindole-1,3(2H)-dione-4,5,6,7-d4, 3a,4,7,7a-tetrahydro-4,7-d2- Catalog No.:AG0006K7 MDL No.: MF:C8H3D6NO2 MW:157.1995	CAS No. 102072-63-9 13-Hexacosenedioic acid, dimethyl ester, (E)- (9CI) Catalog No.:AG0006KM MDL No.: MF:C28H52O4 MW:452.7101	CAS No. 102072-81-1 6-Isoquinolinecarbonitrile, 5,8-dihydro-7-hydroxy-5,8-dioxo- Catalog No.:AG0006KL MDL No.: MF:C10H4N2O3 MW:200.1504
CAS No. 102072-82-2 5,8-Quinoxalinedione, 6,7-dichloro- Catalog No.:AG0006KK MDL No.: MF:C8H2Cl2N2O2 MW:229.0197	CAS No. 102072-84-4 5-Phthalazinamine Catalog No.:AG0006KJ MDL No.:MFCD08272072 MF:C8H7N3 MW:145.1613	CAS No. 1020720-04-0 1,2-Benzisoxazole-4,5,6,7-d4-3-methanesulfonamide Catalog No.:AG0006K6 MDL No.: MF:C8H4D4N2O3S MW:216.2504
CAS No. 1020720-09-5 Benzene-1,2,3,4-d4, 5-bromo-6-nitro- Catalog No.:AG0006K5 MDL No.: MF:C6BrD4NO2 MW:206.0301	CAS No. 1020721-61-2 1H-Pyrazole-5-sulfonyl chloride, 1-methyl- Catalog No.:AG0006K4 MDL No.:MFCD09065021 MF:C4H5ClN2O2S MW:180.6127	CAS No. 1020722-21-7 1H-Indole, 2-(1,1-dimethylethyl)-7-(4-methyl-1-piperazinyl)-4-nitro- Catalog No.:AG0006K3 MDL No.:MFCD09997082 MF:C17H24N4O2 MW:316.3981
CAS No. 1020722-40-0 1H-Pyrazole-5-carboxylic acid, 4-bromo-1,3-diethyl-, ethyl ester Catalog No.:AG0006K2 MDL No.: MF:C10H15BrN2O2 MW:275.1423	CAS No. 1020722-42-2 1H-Pyrazole-5-carboxylic acid, 4-bromo-1,3-diethyl- Catalog No.:AG0006K1 MDL No.: MF:C8H11BrN2O2 MW:247.0891	CAS No. 1020722-48-8 1H-Pyrazole-5-carboxylic acid, 4-bromo-1-ethyl-3-propyl-, ethyl ester Catalog No.:AG0006K0 MDL No.: MF:C11H17BrN2O2 MW:289.1689
CAS No. 1020722-52-4 1H-Pyrazole-5-carboxylic acid, 4-bromo-1-ethyl-3-propyl- Catalog No.:AG0006JZ MDL No.: MF:C9H13BrN2O2 MW:261.1157	CAS No. 1020722-56-8 1H-Pyrazole-5-carboxylic acid, 1-ethyl-3-(2-methylpropyl)-, ethyl ester Catalog No.:AG0006JY MDL No.: MF:C12H20N2O2 MW:224.2994	CAS No. 1020722-62-6 1H-Pyrazole-5-carboxylic acid, 4-bromo-1-methyl-3-(2-methylpropyl)- Catalog No.:AG0006KX MDL No.:MFCD08459083 MF:C9H13BrN2O2 MW:261.1157
CAS No. 1020722-66-0 1H-Pyrazole-5-carboxylic acid, 4-bromo-1-ethyl-3-(2-methylpropyl)- Catalog No.:AG0006KW MDL No.: MF:C10H15BrN2O2 MW:275.1423	CAS No. 1020723-82-3 1H-Pyrazole-5-carboxylic acid, 1-(2,4-difluorophenyl)-3-ethyl- Catalog No.:AG0006KV MDL No.: MF:C12H10F2N2O2 MW:252.2168	CAS No. 1020723-91-4 1H-Pyrazole-5-carboxylic acid, 1-(2,4-difluorophenyl)-3-propyl- Catalog No.:AG0006KU MDL No.: MF:C13H12F2N2O2 MW:266.2434
CAS No. 1020724-01-9 1H-Pyrazole-5-carboxylic acid, 1-(2,4-difluorophenyl)-3-(2-methylpropyl)- Catalog No.:AG0006KT MDL No.: MF:C14H14F2N2O2 MW:280.2700	CAS No. 1020724-10-0 1H-Pyrazole-5-carboxylic acid, 1-(1,1-dimethylethyl)-3-ethyl- Catalog No.:AG0006KS MDL No.: MF:C10H16N2O2 MW:196.2462	CAS No. 1020724-17-7 1H-Pyrazole-5-carboxylic acid, 1-(1,1-dimethylethyl)-3-propyl- Catalog No.:AG0006KR MDL No.: MF:C11H18N2O2 MW:210.2728
CAS No. 1020724-25-7 1H-Pyrazole-5-carboxylic acid, 1-(1,1-dimethylethyl)-3-(2-methylpropyl)- Catalog No.:AG0006KQ MDL No.: MF:C12H20N2O2 MW:224.2994	CAS No. 1020724-40-6 1H-Pyrazole-4-carboxylic acid, 3-(2-methoxyphenyl)-1-methyl-, methyl ester Catalog No.:AG0006KP MDL No.: MF:C13H14N2O3 MW:246.2619	CAS No. 1020743-28-5 8-Quinolinecarbonitrile, 4-bromo- Catalog No.:AG0006KO MDL No.: MF:C10H5BrN2 MW:233.0641
CAS No. 1020743-95-6 1-Propanamine, 2-methoxy-2-methyl-, hydrochloride (1:1) Catalog No.:AG0006KN MDL No.:MFCD20501966 MF:C5H14ClNO MW:139.6238	CAS No. 102077-55-4 Benzene, 1,1'-(1-phenoxyethylidene)bis- Catalog No.:AG0006L2 MDL No.: MF:C20H18O MW:274.3563	CAS No. 102077-60-1 9,10-Anthracenedione, 2-methyl-1-(3-methyl-2-buten-1-yl)- Catalog No.:AG0006L1 MDL No.: MF:C20H18O2 MW:290.3557
CAS No. 102077-86-1 Phenol, 4,4'-[(2-methoxyphenyl)methylene]bis- Catalog No.:AG0006L0 MDL No.: MF:C20H18O3 MW:306.3551	CAS No. 102078-28-4 2-Propen-1-one, 3-phenyl-1-(4,6,7-trimethoxy-5-benzofuranyl)- Catalog No.:AG0006KZ MDL No.: MF:C20H18O5 MW:338.3539	CAS No. 102078-75-1 [1,1'-Biphenyl]-2-carboxamide, N-(phenylmethyl)- Catalog No.:AG0006KY MDL No.: MF:C20H17NO MW:287.3551