A Three-Component Reaction of Aryldiazonium Tetrafluoroborates, Sulfur Dioxide, and 1-(Prop-2-yn-1-yl)indoles under Catalyst-Free Conditions Huajun Chen, Mengli Liu, Guanyinsheng Qiu， and Jie Wua

 

Introduction
As a privileged scaffold, the core of 9H-pyrrolo[1,2-a] indole can be found in many natural products and pharmaceuticals with significant biological activities (Figure 1).[1] For example, compound I is used as a potent antitumor bifunctional DNA alkylating agent.[1a] Excellent antitumor activities are observed as well for compound II (Mitomycin C).[1b–d] Additionally, they act as useful intermediates for the synthesis of complex biologically important compounds.[2] Moreover, 9H-pyrrolo[1,2-a]indoles have been applied in material chemistry, showing unique electrical and optical properties.[3] Thus, extensive efforts have been made for the generation of 9H-pyrrolo[1,2-a]indole scaffold.[4] Among the approaches developed for the construction of 9H-pyrrolo[1,2-a]indole skeleton with a 5-5-6 tricyclic core, most of them focus on the C2-functionality/cyclization of 3-substituted indoles with oxodienes.

On the other hand, the importance of sulfonyl (SO2) moiety in pharmaceuticals and materials is recognized.[6] So far, there are numerous approaches for the synthesis of sulfonyl compounds.[7] Among the methods, generation of sulfonyl compounds through the insertion of sulfur dioxide has proven to be one of the most efficient and straightforward routes.[8] In the past few years, sulfur dioxide surrogate of DABCO · (SO2)2 or inorganic sulfites have been used as a convenient source for the preparation of sulfonyl compounds.[9,10] As part of our continuous efforts in the development of methods for the construction of sulfonyl compounds from sulfur dioxide, we have focused on the radical processes initiated by arylsulfonyl radicals involving sulfur dioxide.[11] The arylsulfonyl radicals could be formed efficiently under metaland additive-free conditions from aryldiazonium tetrafluoroborates DABCO · (SO2)2 or inorganic sulfites.

 

For example, vicinal oxysulfonylation of alkenes could be accomplished from a multi-component reaction of aryldiazonium tetrafluoroborates, alkenes, hydroxyamines with DABCO· (SO2)2 or potassium metabisulfite (K2S2O5).[11b] Prompted by the above results,[11] we envisioned that the arylsulfonyl radical generated in situ from aryldiazonium tetrafluoroborates and DABCO· (SO2)2 might initiate a tandem radical process for the formation of 9H-pyrrolo[1,2-a]indole derivatives. The reaction design is shown in Scheme 1.

 

We conceived that 1-(prop-2-yn-1-yl)indole 1 would be the choice of starting material.[12] Although several reports for the radical reactions of 1-(prop-2-yn-1-yl) indole 1 had been reported,[12] excess amount of oxidant had to be used. In our design, after generation of arylsulfonyl radical from aryldiazonium tetrafluor-oborate 2 and DABCO· (SO2)2, a tandem radical process might occur to form multi-bonds with the formation of 9H-pyrrolo[1,2-a]indole 5-5-6 tricyclic core skeleton. Since tertiary amine (DABCO) radical cation would be released accompanied with arylsulfonyl radical from aryldiazonium tetrafluoroborate 2 and DABCO· (SO2)2,[11] the subsequent oxidative single electron transfer by tertiary amine (DABCO) radical cation would be proceeded under metal catalyst-free conditions. Herein, we report a threecomponent reaction of aryldiazonium tetrafluoroborates, sulfur dioxide surrogate of DABCO · (SO2)2, and 1-(prop-2-yn-1-yl)indoles under catalyst-free conditions. This transformation initiated by arylsulfonyl radical proceeds efficiently in acetonitrile under mild conditions, giving rise to sulfonated 9H-pyrrolo[1,2-a] indoles in moderate to good yields.

 

Results and Discussion
We commenced our studies with a model reaction of 3-methyl-1-(3-(p-tolyl)prop-2-yn-1-yl)-1H-indole 1 a, DABCO· (SO2)2, and 4-methylphenyldiazonium tetrafluoroborate (2 a). Initially, the reaction was performed in THF at 50 8C (Table 1, entry 1). To our delight, the desired product 3 a was afforded in 16% yield. This result encouraged us for further exploration. A higher yield was obtained when the reaction occurred in DMSO or 1,2-dichloroethane (DCE) (Table 1, entries 2 and 3). The corresponding sulfonated 9H-pyrrolo[1,2-a]indole 3 a could be produced in 50% yield when the reaction took place in
acetonitrile (Table 1, entry 4). Since a deprotonation process was proposed to be involved in the transformation, we thus screened several inorganic bases in the reaction at 508C (Table 1, entries 5–7).

 

Gratifyingly, product 3 a was isolated in 61% yield when sodium carbonate (20 mol%) was added (Table 1, entry 7). The reaction was further examined under different temperatures (Table 1, entries 8–10). However, no better results were obtained. The yield was improved when 1.0 equivalent of sodium carbonate was used in the reaction (Table 1, entry 11). Additionally, a gram-scale synthesis of the sulfonated 9Hpyrrolo[1,2-a]indole 3 a was performed in MeCN in the presence of sodium carbonate (1.0 equiv.) (Table 1, entry 12), which provided the corresponding product in 65% yield. No reaction took place when the alkynyl group in substrate 1 a was replaced by an alkenyl group.

The scope generality of this three-component reaction of 1-(prop-2-yn-1-yl)indoles 1, aryldiazonium tetrafluoroborates 2, and sulfur dioxide surrogate of DABCO· (SO2)2 under optimized conditions was then explored. The result presented in Table 2 showed that the method was quite general to provide the corresponding sulfonated 9H-pyrrolo[1,2-a]indoles in moderate to good yields. A range of aryldiazonium tetrafluoroborates 2 was examined, and all reactions proceeded well to produce the desired products.

 

However, the reaction was complex when 4-nitrophenyldiazonium tetrafluoroborate or 4-cyanophenyldiazonium tetrafluoroborate was used as the substrate in the reaction of DABCO· (SO2)2 with 3 methyl-1-(3-(p-tolyl)prop-2-yn-1-yl)-1H-indole 1 a. Additionally, reactions of various 1-(prop-2-yn-1-yl)indoles 1 were explored, which showed the product diversity of this transformation. However, no desired product was detected when methyl 1-(3-phenylprop-2-yn-1-yl)-1Hindole-5-carboxylate or 1-(1-(3-phenylprop-2-yn-1-yl)-1H-indol-3-yl)ethan-1-one was employed in the reaction of DABCO · (SO2)2 and 4-methylphenyldiazonium tetrafluoroborate (2 a). From the results in Table 2, the halo groups attached on the aromatic ring of substrates were all tolerated. In the meantime, the structure of compound 3 g was illustrated by X-ray crystallography analysis (Table 2, also see the Supporting Information).[13] However, no reaction occurred when 1-(4-phenylbut-3-yn-1-yl)-1H-indole was used as
the substrate in the reaction of DABCO · (SO2)2 with 4-methylphenyldiazonium tetrafluoroborate (2 a).

 

Moreover, a reaction of 3-methyl-1-(1-phenyl-3-(ptolyl)prop-2-yn-1-yl)-1H-indole, DABCO · (SO2)2, and 4-methylphenyldiazonium tetrafluoroborate (2 a) was examined. Only a trace amount of product was detected. We postulate that steric hindrance might hamper the reaction process.

Since the reaction was proposed to be proceeded through a tandem radical process, which was triggered by arylsulfonyl radical generated in situ from aryldiazonium tetrafluoroborate 2 and DABCO· (SO2)2, we thus examined the model reaction in Table 1 with the addition of 2.0 equivalent of 2,2,6,6-tetramethyl-1-piperidinyloxy (TEMPO). As expected, the reaction failed to provide the corresponding product 3 a (Scheme 2, eq 1).

A plausible mechanism is shown in Scheme 2. It is known that the combination of DABCO · (SO2)2 with aryldiazonium tetrafluoroborates would provide arylsulfonyl radical A and tertiary amine (DABCO)
radical cation.[11] We postulated that arylsulfonyl radical A would attack the triple bond of 1-(prop-2-yn-1-yl)indole 1, giving rise to alkenyl radical intermediate B. The alkenyl radical intermediate B would subsequently undergo an intramolecular addition of double bond of indole, leading to radical intermediate C. The radical intermediate C would be oxidized to cation D assisted by tertiary amine (DABCO) radical cation via a single electron transfer (SET), with the release of DABCO. The cation D would then proceed through deprotonation in the presence of base (DABCO) to afford intermediate E. Subsequently, tautomerization would occur to produce the desired product 3.

Conclusion
In conclusion, we have reported a three-component reaction of aryldiazonium tetrafluoroborates, sulfur dioxide surrogate of DABCO· (SO2)2, and 1-(prop-2-yn-1-yl)indoles under catalyst-free conditions. This transformation initiated by arylsulfonyl radical proceeds efficiently in acetonitrile under mild conditions, giving rise to sulfonated 9H-pyrrolo[1,2-a]indoles in moderate to good yields. A tandem radical process with the insertion of sulfur dioxide is proposed, with the formation of multi-bonds. The transformation is attractive, since metal catalyst or additive is not necessary in the reaction. Arylsulfonyl radical generated in situ initiates the transformation, and an oxidative single electron transfer is involved in the reaction process.
 

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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. 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. 1020719-23-6 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. 102073-01-8 Bicyclo[4.1.0]hepta-1,3,5-triene-7-carboxaldehyde Catalog No.:AG0006LB MDL No.: MF:C8H6O MW:118.1326
CAS No. 102073-21-2 Thiopyrylium, 2,6-bis(1,1-dimethylethyl)-4-(4-nitrophenyl)-, perchlorate (9CI) Catalog No.:AG0006LA MDL No.: MF:C19H24ClNO6S MW:429.9150	CAS No. 102073-66-5 Stannane, [4-(1,1-dimethylethyl)-1-cyclohexen-1-yl]trimethyl- Catalog No.:AG0006L9 MDL No.: MF:C13H26Sn MW:301.0465	CAS No. 102073-77-8 4-Isoquinolinol, 1,2,3,4-tetrahydro-5,8-dimethoxy- Catalog No.:AG0006L8 MDL No.:MFCD07366383 MF:C11H15NO3 MW:209.2417
CAS No. 102073-95-0 1-Propanamine, 3-chloro-N-(3-chloropropyl)- Catalog No.:AG0006L7 MDL No.:MFCD17012771 MF:C6H13Cl2N MW:170.0801	CAS No. 102074-19-1 3-Pyridinemethanol, 5-methyl- Catalog No.:AG0006L6 MDL No.:MFCD08236816 MF:C7H9NO MW:123.1525	CAS No. 102074-26-0 4-Pyridinol, 2-ethoxy- Catalog No.:AG0006L5 MDL No.: MF:C7H9NO2 MW:139.1519
CAS No. 102074-47-5 1,2-Benzenediamine, 3-chloro-N2-methyl- Catalog No.:AG0006L4 MDL No.:MFCD10694367 MF:C7H9ClN2 MW:156.6128	CAS No. 102074-60-2 4-Pyridinemethanol, 3-methoxy- Catalog No.:AG0006L3 MDL No.:MFCD16606979 MF:C7H9NO2 MW:139.1519	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
CAS No. 102089-75-8 Carbamic acid, N-[(1R)-2-[(methylsulfonyl)oxy]-1-phenylethyl]-, 1,1-dimethylethyl ester Catalog No.:AG0006LQ MDL No.: MF:C14H21NO5S MW:315.3852	CAS No. 102090-59-5 Carbamic acid, [2-hydroxy-2-(2-thienyl)ethyl]-, 1,1-dimethylethyl ester (9CI) Catalog No.:AG0006LP MDL No.: MF:C11H17NO3S MW:243.3226	CAS No. 102091-40-7 1-Octadecanamine, N-hexadecyl-N-methyl- Catalog No.:AG0006LO MDL No.: MF:C35H73N MW:507.9608
CAS No. 102091-56-5 Indium, ethyldimethyl- Catalog No.:AG0006LN MDL No.: MF:C4H11In MW:173.9481	CAS No. 102092-23-9 Benzoic acid, 3-chloro-6-hydroxy-4-methoxy-2-methyl-, (2R,4S,4aR,7aS,7bR)-2,4,4a,5,6,7,7a,7b-octahydro-4-hydroxy-3-(hydroxymethyl)-6,6,7b-trimethyl-1H-cyclobut[e]inden-2-yl ester Catalog No.:AG0006LM MDL No.: MF:C24H31ClO6 MW:450.9523	CAS No. 102092-31-9 2,6-Piperidinedione, 1-[(octahydro-7-hydroxy-2H-quinolizin-1-yl)methyl]-, [1R-(1α,7α,9aα)]- (9CI) Catalog No.:AG0006LL MDL No.: MF: MW:
CAS No. 102092-44-4 Benzoic acid, 2-hydroxy-4-methoxy-6-methyl-, 2,4,4a,5,6,7,7a,7b-octahydro-4-hydroxy-3-(hydroxymethyl)-6,6,7b-trimethyl-1H-cyclobut[e]inden-2-yl ester, [2R-(2α,4α,4aα,7aα,7bβ)]- Catalog No.:AG0006LK MDL No.: MF:C24H32O6 MW:416.5073	CAS No. 102092-51-3 Methanone, (3-bromophenyl)(4-methylphenyl)- Catalog No.:AG0006LJ MDL No.:MFCD06201458 MF:C14H11BrO MW:275.1405	CAS No. 102093-68-5 1,3-Benzenediamine,4-methyl-2,6-bis(methylthio)- Catalog No.:AG0006LI MDL No.: MF:C9H14N2S2 MW:214.3509
CAS No. 102093-85-6 Carbonochloridic acid, 2-[(4-nitrophenyl)sulfonyl]ethyl ester Catalog No.:AG0006LH MDL No.: MF:C9H8ClNO6S MW:293.6809	CAS No. 1020939-55-2 2-Pyridinemethanamine, N-(3-methoxyphenyl)- Catalog No.:AG0006LE MDL No.: MF:C13H14N2O MW:214.2631	CAS No. 1020954-12-4 Hydrazine, [1-(3-chloro-4-fluorophenyl)ethyl]- Catalog No.:AG0006LD MDL No.: MF:C8H10ClFN2 MW:188.6298
CAS No. 1020955-20-7 5-Isoxazolamine, 3-(4-ethylphenyl)- Catalog No.:AG0006LC MDL No.:MFCD07382879 MF:C11H12N2O MW:188.2258	CAS No. 102096-20-8 2-Butanone, 1-[(methylsulfonyl)oxy]- Catalog No.:AG0006LG MDL No.: MF:C5H10O4S MW:166.1955	CAS No. 102096-25-3 Propanoic acid, 2-Methyl-, 2,2,2-trifluoroethyl ester Catalog No.:AG0006LF MDL No.: MF:C6H9F3O2 MW:170.1297