Formal [4 + 1] Cycloaddition of o-Aminobenzyl Chlorides with Isocyanides: Synthesis of 2-Amino-3-Substituted Indoles

 

Jacobus A. W. Jong,a Xu Bao,a Qian Wang,a and Jieping Zhu*a
a Laboratory of Synthesis and Natural Products, Institute of Chemical Sciences and Engineering, Ecole Polytechnique Fédérale de Lausanne, EPFL-SB-ISIC-LSPN, BCH5304, CH-1015 Lausanne (Switzerland), e-mail: jieping.zhu@epfl.ch

Dedicated to Prof. Fran?ois  Diederich

 

 

Introduction
2-Aminoindole is an important structural motif found frequently in natural products and pharmaceuticals. Cryptotackieine[1,2] and perophoramidine[3] are repre- sentative indoloquinoline alkaloids that contain such a structural subunit. While many powerful  reactions  have been developed for the synthesis of indoles,[4] synthetic methods allowing efficient construction of 2- aminoindoles  remained  limited.[5 – 11] Listed in Scheme 1 are some of the recently developed method- ologies including 1) Pd-catalyzed Buchwald– Hartwig N-arylation  of   2-haloindoles   with   anilines   (Sche-   me 1,a);[12,13] 2) Pd-catalyzed heteroannulation of N- alkynyl-2-haloanilides with amines (Scheme 1,b);[14] 3) Pd-catalyzed coupling of ynamides and o-iodoanilines (Scheme 1,c);[15] 4) Pd-catalyzed domino N-arylation followed by base-promoted cyclization (Scheme  1,d);[16] 5)copper-catalyzed reaction of substituted N-(2- halophenyl)-2,2,2-trifluoroacetamides with alkyl 2-cya- noacetate or malononitrile (Scheme 1,e);[17] 6) gold- catalyzed intermolecular reaction of azides with ynamides (Scheme 1,f).[18,19] In spite of these significant achievements, the development of practical and cost-effective methods are still highly demanding. Indeed, most of the recently developed 2-aminoindole syn- thesis relied on the expensive transition metals.

 

Isocyanide, by virtue of its carbene-like reactivity, has been widely used as a key component in the development of novel multicomponent reactions.[20 – 26] The capability of isocyanide to undergo an α-addition with both an electrophile and a nucleophile also made it an ideal one  carbon synthon[27 – 29] that has been extensively exploited in a broad range of cycloaddition reactions including [4 +
1],[30,31] [3 + 1],[32 – 34] [5 + 1],[35 – 40] and [2 + 2 + 1][41,42] cycloaddition reactions, and radical addition proc- esses.[43] More relevant to the present topic, a number  of  valuable  synthetic  methodologies  have  also  been developed for the synthesis of indoles using aryliso- cyanides as starting materials.[44]

 

Our group has a long-term interest in isocyanide chemistry[45 – 52] and has reported an AlCl3-catalyzed formal [4 + 1] cycloaddition of 2-cyano-1-azadienes with isocyanides for the synthesis of 2-amino-5- cyanopyrroles.[53] As a continuation of this research program, we report herein a novel synthesis of 2- aminoindoles 3 by a base-promoted (NaHCO3) reaction of N-tosyl-2-aminobenzyl chlorides 1 with isocya- nides  2  (Scheme 1,g). While  isocyanide-based formal [4+ 1] cycloadditions have been employed for the syn- thesis of diverse heterocycles,[30]  its application to the synthesis of indoles was, to the best of our knowledge, unprecedented. We note that Xiao and co-workers  have reported an elegant synthesis of 2-acylindoles by reaction of 1 with sulfur ylides.[54]

 

Results and Discussion
Our initial efforts to find suitable reaction conditions were pursued using tBuNC (2a) and N-{2-[chloro- (phenyl)methyl]phenyl}-4-methylbenzene-1-sulfon- amide (1a) as testing substrates (Table 1). The con- ditions were optimized by varying systematically the bases, the solvents, the temperature, and the reaction time. Key observations are summarized as follows: 1) NaHCO3 was a base of choice among those screened (Cs2CO3, NaOH, MeONa, NaHCO3, Na2CO3, K2CO3, Et3N, DBU, Entries 1 – 8). In the absence of base, the reaction gave the desired product  with much lower yield (Entry 9); 2) Using NaHCO3  as base, CH2Cl2  turned  out to be the best solvent (Entries 4, 10 – 14); 3) Reaction was best performed at room temperature (Entries 4 vs. 15). The structure of 3a was confirmed by X-ray crystallographic analysis. It is very stable and can be stored at room temperature for months without degradation.

 

With the optimal reaction conditions in hand, the scope of this novel 2-amino-3-substituted indole syn- thesis was examined. The o-aminobenzyl chlorides 1 and isocyanides 2 used in this study were listed in Figure 1. As shown in Scheme 2, the reaction of tBuNC (2a), BuNC (2b), 4-methoxyphenylisocyanide (2c), and 2,6-dimethylphenylisocyanide (2d) with N-{2-[chloro- (phenyl)methyl]phenyl}-4-methylbenzene-1-sulfon- amide (1a) afforded the corresponding 2-amino-3- phenylindoles (3a, 3b, 3c, 3d) in moderate to good yields. Functionalized isocyanides such as methyl α- isocyanoacetate (2e) and α-isocyanocarboxamides (2f, 2g)[55] participated in the reaction to afford the corresponding products (3e – 3g). It is interesting to note that in the case of 2f and 2g, the competitive formation of oxazole was not observed.[56,57] The  2- alkyl substituted o-aminobenzyl chlorides 1b and 1c reacted with alkyl, aryl, and functionalized isocyanides to provide the corresponding 2-amino-3-alkyl substi- tuted indoles (3h – 3j) in good yields. Chloro- and nitro-substituted N-tosyl-o-aminobenzyl chlorides 1d and 1e reacted with tBuNC (2a) to give the indoles 3k and 3l in 83 % and 67 % yield, respectively. The N-(p- nitrophenyl)sulfonyl and N-(o-nitrophenyl)sulfonyl pro- tected o-aminobenzyl chlorides 1f and 1g participated in the reaction to furnish the 2-aminoindoles 3m – 3o  in good to excellent yields. The cyclic carbamate of  type 1i (Figure 1) is also known to be a suitable precursor of aza-ortho-xylylene and has been success- fully used in the synthesis of complex natural prod- uct.[58] However, no reaction occurred when 1i and 2a was treated under standard reaction conditions due to the high stability of 1i. Heating the mixture led only to the decomposition of the reactants.
Interestingly, the reaction of N-[2-(chloromethyl)- phenyl]-4-methylbenzene-1-sulfonamide (1h) with tBuNC (2a) under the standard conditions afforded, after 1 h, compound 3p in 66 % yield resulting most probably from the nucleophilic attack of the so formed 2-aminoindole to the second molecule of 1h (Scheme 3). Finally, the indole N-Nos group of 3m can  be easily removed to provide the indole N-unpro- tected product 3q in 72 % yield (Scheme 3).

 

A possible reaction pathway accounting for the formation of 2-aminoindole 3 is depicted in Scheme 4. The reaction was thought to be initiated by the base- promoted elimination of HCl from N-(ortho-chloro- methyl)aryl amide 1 leading to the aza-ortho-xylylene intermediate A.[59,60] Nucleophilic addition of the isocyanide to the benzylic carbon of A  would  afford the nitrilium intermediate B which underwent a facile cyclization to furnish the cyclic amidine C. Tautomeri- zation of the later would deliver then the 2-amino- indole 3.

Conclusion
In summary, we described herein the first examples of NaHCO3-promoted formal [4 + 1] cycloaddition be- tween isocyanides and N-(ortho-chloromethyl)aryl amides. The reaction proceeded at room temperature to afford the 2-aminoindoles in good to high yields. Mild  conditions,  high  yields,  and  simple experimental
procedures characterized the  present indole  synthesis.

Experimental Section
General Procedure
To a solution of the N-arylsulfonyl o-aminobenzyl chloride 1 (0.1 mmol, 1.0 equiv.) in CH2Cl2  (1.5 mL) were added NaHCO3 (42 mg, 0.5 mmol, 5.0 equiv.) and the isocyanide 2 (3.0 equiv.). The resulting mixture was stirred at room temperature until the completion  of  the reaction. The solution was diluted with CH2Cl2 and washed with water. The organic layer was dried over Na2SO4 and evaporated to dryness. The residue was purified by column chromatography on silica gel to give the 2-aminoindole 3.

Acknowledgements
We thank EPFL (Switzerland) and the Swiss National Science Foundation (SNSF 20020-155973) for financial support. We thank Dr. F.-T. Farzaneh and Dr. Rosario Scopelliti for the X-ray structural analysis of compound 3a. J. A. W. J. is an exchange Master student from the Vrije Universiteit Amsterdam, Netherlands.

Author Contribution Statement
J. A. W. J., X. B., Q. W., and J. Z. conceived and designed the experiments. J. A. W. J., X. B. carried out the experiments. J. A. W. J., X. B., Q. W., and J. Z. interpreted the results and co-wrote the manuscript.

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CAS No. 102433-47-6 Urea, N-(2-chloroethyl)-N'-[2-phenyl-1-(phenylmethyl)ethyl]- Catalog No.:AG0007GJ MDL No.: MF:C18H21ClN2O MW:316.8251	CAS No. 102433-48-7 Urea, N-(2-chloroethyl)-N'-(4-ethylphenyl)- Catalog No.:AG0007GI MDL No.: MF:C11H15ClN2O MW:226.7026	CAS No. 102433-50-1 Urea, N-(2-chloroethyl)-N'-(5-hydroxy-1-naphthalenyl)- Catalog No.:AG0007GH MDL No.: MF:C13H13ClN2O2 MW:264.7075
CAS No. 102433-53-4 Urea, N-(2-chloroethyl)-N'-(2-methyl-1-phenylpropyl)- Catalog No.:AG0007GG MDL No.: MF:C13H19ClN2O MW:254.7558	CAS No. 102433-54-5 Urea, N-(2-chloroethyl)-N'-(6-methoxy-2-benzothiazolyl)- Catalog No.:AG0007GF MDL No.: MF:C11H12ClN3O2S MW:285.7499	CAS No. 102433-58-9 Urea, N'-(2-chloroethyl)-N-methyl-N-(5,6,7,8-tetrahydro-1-naphthalenyl)- Catalog No.:AG0007GE MDL No.: MF:C14H19ClN2O MW:266.7665
CAS No. 102433-59-0 Urea, N-(2-chloroethyl)-N'-(5,6,7,8-tetrahydro-4-methyl-1-naphthalenyl)- Catalog No.:AG0007GD MDL No.: MF:C14H19ClN2O MW:266.7665	CAS No. 102433-61-4 Urea, N-(2-chloroethyl)-N'-[3-(methylthio)phenyl]- Catalog No.:AG0007GC MDL No.:MFCD01676609 MF:C10H13ClN2OS MW:244.7410	CAS No. 102433-64-7 Urea, N-(2-chloroethyl)-N'-(1-methyl-3-phenylpropyl)- Catalog No.:AG0007GB MDL No.: MF:C13H19ClN2O MW:254.7558
CAS No. 102433-65-8 Urea, N-(2-chloroethyl)-N'-(2-propylphenyl)- Catalog No.:AG0007HO MDL No.: MF:C12H17ClN2O MW:240.7292	CAS No. 102433-66-9 Urea, N-(2-chloroethyl)-N'-(1,2,3,4-tetrahydro-2-naphthalenyl)- Catalog No.:AG0007HN MDL No.: MF:C13H17ClN2O MW:252.7399	CAS No. 102433-68-1 Urea, N-(2-chloroethyl)-N'-(5,6,7,8-tetrahydro-1-naphthalenyl)- Catalog No.:AG0007HM MDL No.: MF:C13H17ClN2O MW:252.7399
CAS No. 102433-69-2 Urea, N-(2-chloroethyl)-N'-[(5,6,7,8-tetrahydro-1-naphthalenyl)methyl]- Catalog No.:AG0007HL MDL No.: MF:C14H19ClN2O MW:266.7665	CAS No. 102433-70-5 Urea, N-(2-chloroethyl)-N'-(2,3,5,6-tetramethylphenyl)- Catalog No.:AG0007HK MDL No.: MF:C13H19ClN2O MW:254.7558	CAS No. 102433-71-6 Urea, N-(2-chloroethyl)-N'-2H-tetrazol-5-yl- Catalog No.:AG0007HJ MDL No.: MF:C4H7ClN6O MW:190.5910
CAS No. 102433-76-1 Urea, N-(2-chloropropyl)-N'-(5,6,7,8-tetrahydro-1-naphthalenyl)- Catalog No.:AG0007HI MDL No.: MF:C14H19ClN2O MW:266.7665	CAS No. 102433-77-2 1,2,4-Triazolidine-1,3-dicarboxylic acid, 3-benzoyl-5-phenyl-4-(phenylmethyl)-, 1,3-diethyl ester Catalog No.:AG0007HH MDL No.: MF:C28H29N3O5 MW:487.5470	CAS No. 102433-78-3 3,4,5-Pyridinetricarbonitrile, 2-amino-6-methoxy- Catalog No.:AG0007HG MDL No.: MF:C9H5N5O MW:199.1689
CAS No. 102434-00-4 Urea, N-(2-chloroethyl)-N'-[2-(2-propen-1-yl)phenyl]- Catalog No.:AG0007HF MDL No.: MF:C12H15ClN2O MW:238.7133	CAS No. 102434-02-6 Urea, N-1-anthracenyl-N'-(2-bromoethyl)- Catalog No.:AG0007HE MDL No.: MF:C17H15BrN2O MW:343.2178	CAS No. 102434-03-7 Urea, N-1-anthracenyl-N'-(2-chloroethyl)- Catalog No.:AG0007HD MDL No.: MF:C17H15ClN2O MW:298.7668
CAS No. 102434-05-9 Urea, N-1,3-benzodioxol-5-yl-N'-(2,6-dimethylphenyl)- Catalog No.:AG0007HC MDL No.: MF:C16H16N2O3 MW:284.3098	CAS No. 102434-06-0 Urea, N-2-benzothiazolyl-N,N'-dimethyl-N'-nitroso- Catalog No.:AG0007HB MDL No.: MF:C10H10N4O2S MW:250.2770	CAS No. 102434-10-6 Urea, N-[1,1'-biphenyl]-2-yl-N'-(2-chloroethyl)- Catalog No.:AG0007HA MDL No.: MF:C15H15ClN2O MW:274.7454
CAS No. 102434-11-7 Urea, N,N-bis(2-bromoethyl)-N'-1-naphthalenyl- Catalog No.:AG0007H9 MDL No.: MF:C15H16Br2N2O MW:400.1083	CAS No. 102434-19-5 Urea, N-(2-bromoethyl)-N'-(3-bromo-2-naphthalenyl)- Catalog No.:AG0007H8 MDL No.: MF:C13H12Br2N2O MW:372.0552	CAS No. 102434-20-8 Urea, N-(2-bromoethyl)-N'-(4-chloro-1-naphthalenyl)- Catalog No.:AG0007H7 MDL No.: MF:C13H12BrClN2O MW:327.6042
CAS No. 102434-23-1 Urea, N-(2-bromoethyl)-N'-(2-ethoxy-1-naphthalenyl)- Catalog No.:AG0007H6 MDL No.: MF:C15H17BrN2O2 MW:337.2117	CAS No. 102434-25-3 Urea, N-(2-bromoethyl)-N-ethyl-N'-1-naphthalenyl- Catalog No.:AG0007H5 MDL No.: MF:C15H17BrN2O MW:321.2123	CAS No. 102434-29-7 Urea, N'-(2-bromoethyl)-N-methyl-N-1-naphthalenyl- Catalog No.:AG0007H4 MDL No.: MF:C14H15BrN2O MW:307.1857
CAS No. 102434-30-0 Urea, N-(2-bromoethyl)-N'-[(2-methyl-1-naphthalenyl)methyl]- Catalog No.:AG0007H3 MDL No.: MF:C15H17BrN2O MW:321.2123	CAS No. 102434-32-2 Urea, N-(2-bromoethyl)-N'-[2-(1-naphthalenyl)ethyl]- Catalog No.:AG0007H2 MDL No.: MF:C15H17BrN2O MW:321.2123	CAS No. 102434-35-5 Urea, N-(2-bromoethyl)-N'-8-quinolinyl- Catalog No.:AG0007H1 MDL No.: MF:C12H12BrN3O MW:294.1472
CAS No. 102434-36-6 Urea, N-(2-bromoethyl)-N'-(5,6,7,8-tetrahydro-2-naphthalenyl)- Catalog No.:AG0007H0 MDL No.: MF:C13H17BrN2O MW:297.1909	CAS No. 102434-37-7 Urea, N-(2-bromoethyl)-N'-[2-(trifluoromethyl)phenyl]- Catalog No.:AG0007I8 MDL No.: MF:C10H10BrF3N2O MW:311.0984	CAS No. 102434-38-8 Urea, N-(3-bromopropyl)-N'-1-naphthalenyl- Catalog No.:AG0007I7 MDL No.: MF:C14H15BrN2O MW:307.1857
CAS No. 102434-43-5 Urea, N-9H-carbazol-9-yl-N'-(2-chloroethyl)- Catalog No.:AG0007I6 MDL No.: MF:C15H14ClN3O MW:287.7442	CAS No. 102434-78-6 Benzene, 1,1'-(3-chloro-3-methylbutylidene)bis[4-methyl- (9CI) Catalog No.:AG0007I5 MDL No.: MF:C19H23Cl MW:286.8389	CAS No. 102435-72-3 Bicyclo[2.2.2]octane, 2,2-dimethyl-3-methylene- Catalog No.:AG0007I4 MDL No.: MF:C11H18 MW:150.2606
CAS No. 102436-59-9 Zinc(1+), dichloro- (9CI) Catalog No.:AG0007I3 MDL No.: MF:Cl2Zn+ MW:136.2860	CAS No. 1024368-23-7 Acetic acid, 2-[[3-chloro-5-(trifluoromethyl)-2-pyridinyl]thio]-, methyl ester Catalog No.:AG0007HP MDL No.:MFCD00245199 MF:C9H7ClF3NO2S MW:285.6706	CAS No. 102437-79-6 Benzene, 1,2-bis(azidomethyl)- Catalog No.:AG0007I2 MDL No.: MF:C8H8N6 MW:188.1893
CAS No. 102437-80-9 Benzene, 1,3-bis(azidomethyl)- Catalog No.:AG0007I1 MDL No.: MF:C8H8N6 MW:188.1893	CAS No. 102437-90-1 1,4-Oxathiin-2-acetamide, 5,6-dihydro-N-phenyl- Catalog No.:AG0007I0 MDL No.: MF:C12H13NO2S MW:235.3021	CAS No. 102438-16-4 2-Hexynoic acid, 6-(phenylmethoxy)-, methyl ester Catalog No.:AG0007HZ MDL No.: MF:C14H16O3 MW:232.2750
CAS No. 102438-50-6 5-Hexen-1-ol, 6-(phenylthio)-, (5E)- Catalog No.:AG0007HY MDL No.: MF:C12H16OS MW:208.3198	CAS No. 102438-65-3 2-Hexanone, 5-chloro- Catalog No.:AG0007HX MDL No.: MF:C6H11ClO MW:134.6039	CAS No. 102438-91-5 2-Pyridinemethanol, 3-propyl- Catalog No.:AG0007HW MDL No.: MF:C9H13NO MW:151.2056
CAS No. 102438-98-2 Benzenamine, 2,4-dimethoxy-6-methyl- Catalog No.:AG0007HV MDL No.:MFCD11845581 MF:C9H13NO2 MW:167.2050	CAS No. 102438-99-3 Benzenamine, 2,4,6-trimethoxy-, hydrochloride (1:1) Catalog No.:AG0007HU MDL No.:MFCD00211326 MF:C9H14ClNO3 MW:219.6654	CAS No. 102439-33-8 Benzenamine, 2-ethoxy-5-methoxy- Catalog No.:AG0007HT MDL No.:MFCD09736306 MF:C9H13NO2 MW:167.2050
CAS No. 102439-64-5 1,5-Pentanediol, 3-methyl-3-propyl- Catalog No.:AG0007HS MDL No.: MF:C9H20O2 MW:160.2539	CAS No. 102439-69-0 1,2,3-Nonanetriol Catalog No.:AG0007HR MDL No.: MF:C9H20O3 MW:176.2533	CAS No. 10244-04-9 1,4-Thiazepine, 5-ethoxy-2,3,6,7-tetrahydro- Catalog No.:AG0007ID MDL No.: MF:C7H13NOS MW:159.2492
CAS No. 10244-23-2 2,4-Pyrimidinediamine, 6-chloro-N2,N2,N4,N4-tetraethyl- Catalog No.:AG0007IC MDL No.: MF:C12H21ClN4 MW:256.7749	CAS No. 10244-24-3 Morpholine, 4,4'-(6-chloro-2,4-pyrimidinediyl)bis- Catalog No.:AG0007IB MDL No.:MFCD01873150 MF:C12H17ClN4O2 MW:284.7420	CAS No. 10244-77-6 3H-Pyrazol-3-one, 2,4-dihydro-4-(2-hydroxyethyl)-5-phenyl- Catalog No.:AG0007IA MDL No.: MF:C11H12N2O2 MW:204.2252
CAS No. 10244-78-7 5(4H)-Isoxazolone, 4-(2-hydroxyethyl)-3-methyl- Catalog No.:AG0007I9 MDL No.: MF:C6H9NO3 MW:143.1406	CAS No. 102440-24-4 1H-Pyrrole-3-carboxylic acid, 2-methyl-4-(1-methylethyl)- Catalog No.:AG0007HQ MDL No.: MF:C9H13NO2 MW:167.2050	CAS No. 102440-39-1 Propanenitrile, 3-[[3-(4-morpholinyl)propyl]amino]- Catalog No.:AG0007IZ MDL No.:MFCD01566865 MF:C10H19N3O MW:197.2774
CAS No. 102441-39-4 1H-Indole-3-ethanamine, β,2-diphenyl- Catalog No.:AG0007IY MDL No.:MFCD03988751 MF:C22H20N2 MW:312.4076	CAS No. 102443-38-9 Benzenamine, 4,4'-(diethoxymethylene)bis[N,N-dimethyl- Catalog No.:AG0007IX MDL No.: MF:C21H30N2O2 MW:342.4751	CAS No. 102444-65-5 Borane, tricycloheptyl- Catalog No.:AG0007IW MDL No.: MF:C21H39B MW:302.3454
CAS No. 102445-18-1 Phenol, 4,4'-nonylidenebis- Catalog No.:AG0007IV MDL No.: MF:C21H28O2 MW:312.4458	CAS No. 102446-17-3 Pyrrolidine, 1-butyl-3-[(4-chlorophenyl)phenylmethoxy]- Catalog No.:AG0007IU MDL No.: MF:C21H26ClNO MW:343.8902	CAS No. 102446-20-8 Pyrrolidine, 3-[(4-chlorophenyl)phenylmethoxy]-1-(2-methylpropyl)-, hydrochloride (1:1) Catalog No.:AG0007IT MDL No.: MF:C21H27Cl2NO MW:380.3512
CAS No. 102447-89-2 1,3-Propanediol, 2-methyl-2-propyl-, 1,3-dibenzoate Catalog No.:AG0007IS MDL No.: MF:C21H24O4 MW:340.4129	CAS No. 102449-21-8 9H-Fluorene-9-carboxylic acid, 2-(1-methyl-2-pyrrolidinyl)ethyl ester Catalog No.:AG0007IR MDL No.: MF:C21H23NO2 MW:321.4128	CAS No. 102449-34-3 1-Piperidinecarboxylic acid, 4-(diphenylmethylene)-, ethyl ester Catalog No.:AG0007IQ MDL No.: MF:C21H23NO2 MW:321.4128
CAS No. 102449-89-8 Benzoic acid, 3,3'-dithiobis[4-amino- Catalog No.:AG0007IP MDL No.:MFCD20441327 MF:C14H12N2O4S2 MW:336.3861	CAS No. 10245-44-0 4-Pyridinecarboxylic acid, 2-(1H-indol-3-ylmethylene)hydrazide Catalog No.:AG0007J2 MDL No.: MF:C15H12N4O MW:264.2820	CAS No. 10245-72-4 Benzo[b]thiophene-3-propanoic acid, 2-bromo- Catalog No.:AG0007J1 MDL No.: MF:C11H9BrO2S MW:285.1570
CAS No. 10245-82-6 1H-Pyrrole, 2-(3,5-dibromo-2-methoxyphenyl)- Catalog No.:AG0007J0 MDL No.: MF:C11H9Br2NO MW:331.0033	CAS No. 102450-00-0 Cyclohexaneethanamine, 2-methyl- Catalog No.:AG0007IO MDL No.:MFCD07772984 MF:C9H19N MW:141.2539	CAS No. 102450-20-4 3-Piperidinemethanol, 1-propyl- Catalog No.:AG0007IN MDL No.:MFCD16153150 MF:C9H19NO MW:157.2533
CAS No. 102450-37-3 Cycloheptane, 1,1-dibromo- Catalog No.:AG0007IM MDL No.: MF:C7H12Br2 MW:255.9782	CAS No. 102450-66-8 Heptanoic acid, 2-amino-3-ethyl- Catalog No.:AG0007IL MDL No.: MF:C9H19NO2 MW:173.2527	CAS No. 102450-96-4 Carbamic acid, hexyl-, oxiranylmethyl ester (9CI) Catalog No.:AG0007IK MDL No.: MF:C10H19NO3 MW:201.2628
CAS No. 102451-89-8 Ethanone, 1-[2-(benzoyloxy)-3-iodo-4-(phenylmethoxy)phenyl]- Catalog No.:AG0007IJ MDL No.: MF:C22H17IO4 MW:472.2724	CAS No. 102454-61-5 Benzene, 1,1'-[1,4-butanediylbis(oxy)]bis[4-(ethylthio)- (9CI) Catalog No.:AG0007II MDL No.: MF:C20H26O2S2 MW:362.5492	CAS No. 102454-96-6 1,4-Butanediol, 1,4-bis(3,4-dimethoxyphenyl)- Catalog No.:AG0007IH MDL No.: MF:C20H26O6 MW:362.4168
CAS No. 102456-48-4 Stannane, tributyl-1H-inden-1-yl- Catalog No.:AG0007IG MDL No.: MF:C21H34Sn MW:405.1957	CAS No. 102458-70-8 Piperidine, 2-[(3,4-dimethoxyphenyl)methyl]- Catalog No.:AG0007IF MDL No.: MF:C14H21NO2 MW:235.3220	CAS No. 1024583-33-2 6-Benzothiazolecarboxylic acid, 2-bromo-, methyl ester Catalog No.:AG0007IE MDL No.:MFCD16660646 MF:C9H6BrNO2S MW:272.1184
CAS No. 1024589-68-1 Pyrrolidine, 1-(3-azetidinyl)-, hydrochloride (1:2) Catalog No.:AG0007JG MDL No.:MFCD11617821 MF:C7H16Cl2N2 MW:199.1213	CAS No. 102459-02-9 3-Piperidinemethanamine, 1-ethyl- Catalog No.:AG0007JN MDL No.:MFCD07757606 MF:C8H18N2 MW:142.2419	CAS No. 1024590-32-6 1-Pyrrolidinecarboxylic acid, 3-(4-pyridinyl)-, 1,1-diMethylethyl ester Catalog No.:AG0007JF MDL No.:MFCD25542384 MF:C14H20N2O2 MW:248.3208
CAS No. 1024594-86-2 Thieno[3,4-b]thiophene-2-carboxylic acid, 4,6-dibromo- Catalog No.:AG0007JE MDL No.:MFCD19440952 MF:C7H2Br2O2S2 MW:342.0276	CAS No. 1024598-01-3 Indolo[2,3-a]carbazole, 11-(4,6-diphenyl-1,3,5-triazin-2-yl)-11,12-dihydro-12-phenyl- Catalog No.:AG0007JD MDL No.: MF:C39H25N5 MW:563.6493	CAS No. 1024598-06-8 Indolo[2,3-a]carbazole, 11,12-dihydro-11-phenyl- Catalog No.:AG0007JC MDL No.:MFCD22581305 MF:C24H16N2 MW:332.3972
CAS No. 10246-16-9 Acetamide, N-(2-furanylmethyl)-N-(2-hydroxyethyl)- Catalog No.:AG0007JQ MDL No.: MF:C9H13NO3 MW:183.2044	CAS No. 10246-17-0 Acetamide, N-(2-hydroxyethyl)-N-[(5-methyl-2-furanyl)methyl]- Catalog No.:AG0007JP MDL No.: MF:C10H15NO3 MW:197.2310	CAS No. 10246-68-1 Nonanoic acid, compd. with 2,2',2''-nitrilotris[ethanol] (1:1) Catalog No.:AG0007JO MDL No.: MF:C15H33NO5 MW:307.4262
CAS No. 1024604-94-1 Spiro[2H-1-benzopyran-2,4'-piperidine]-1'-carboxylic acid, 3,4-dihydro-4-hydroxy-, 1,1-diMethylethyl ester Catalog No.:AG0007JB MDL No.:MFCD22377049 MF:C18H25NO4 MW:319.3954	CAS No. 1024605-79-5 Cyclopropanamine, 2-(3-pyridinyl)-, hydrochloride (1:1) Catalog No.:AG0007JA MDL No.: MF:C8H11ClN2 MW:170.6393	CAS No. 102461-06-3 Cyclohexanamine, N-(3-methyl-2(3H)-benzothiazolylidene)- Catalog No.:AG0007JM MDL No.: MF:C14H18N2S MW:246.3711
CAS No. 1024612-25-6 1H-Indol-4-ol, 3-[2-[methyl(1-methylethyl)amino]ethyl]-, 4-acetate Catalog No.:AG0007J9 MDL No.: MF:C16H22N2O2 MW:274.3581	CAS No. 1024613-61-3 Benzeneacetic acid, α-amino-4-methoxy-3-methyl- Catalog No.:AG0007J8 MDL No.: MF:C10H13NO3 MW:195.2151	CAS No. 1024616-26-9 2-Hexenamide, N-cyclopropyl- Catalog No.:AG0007J7 MDL No.:MFCD11865327 MF:C9H15NO MW:153.2215
CAS No. 1024618-29-8 Cyclohexanecarboxylic acid, 2-amino-, methyl ester, hydrochloride (1:1), (1R,2R)- Catalog No.:AG0007J6 MDL No.:MFCD13195006 MF:C8H16ClNO2 MW:193.6711	CAS No. 1024618-84-5 2-Piperazineacetic acid, 1-(1-methylethyl)-3-oxo- Catalog No.:AG0007J5 MDL No.:MFCD05870470 MF:C9H16N2O3 MW:200.2349	CAS No. 102464-38-0 1,3,5-Triazine-2,4-diamine, N2,N2,N4-tributyl-6-(1-piperidinyl)- Catalog No.:AG0007JL MDL No.: MF:C20H38N6 MW:362.5559
CAS No. 1024677-77-7 1,3,2-Dioxaborolane, 2-(5-ethyl-2-furanyl)-4,4,5,5-tetramethyl- Catalog No.:AG0007J4 MDL No.:MFCD12032490 MF:C12H19BO3 MW:222.0885	CAS No. 1024677-85-7 1H-Indole-1-carboxylic acid, 5-bromo-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-, 1,1-dimethylethyl ester Catalog No.:AG0007J3 MDL No.:MFCD12407263 MF:C19H25BBrNO4 MW:422.1211	CAS No. 102468-57-5 2-Propen-1-one, 1-[4-(benzoyloxy)phenyl]-3-phenyl- Catalog No.:AG0007JK MDL No.: MF:C22H16O3 MW:328.3606
CAS No. 102468-65-5 4H-1-Benzopyran-4-one, 3-hydroxy-2-[4-(phenylmethoxy)phenyl]- Catalog No.:AG0007JJ MDL No.: MF:C22H16O4 MW:344.3600	CAS No. 102468-79-1 1-Propanone, 1-(4-bromophenyl)-3-phenyl-3-(phenylthio)- Catalog No.:AG0007JI MDL No.: MF:C21H17BrOS MW:397.3281	CAS No. 102469-08-9 Benzenamine, N-[[4-(2-phenylethenyl)phenyl]methylene]- Catalog No.:AG0007JH MDL No.: MF:C21H17N MW:283.3664
CAS No. 102469-36-3 2,5-Pyrrolidinedione, 1-(2-naphthalenyl)-3-(phenylmethyl)- Catalog No.:AG0007K9 MDL No.: MF:C21H17NO2 MW:315.3652	CAS No. 102469-74-9 Benzenamine, 4-(4,5-diphenyl-1H-imidazol-2-yl)- Catalog No.:AG0007K8 MDL No.: MF:C21H17N3 MW:311.3798	CAS No. 10247-46-8 D-Fructofuranose Catalog No.:AG0007KF MDL No.: MF:C6H12O6 MW:180.1559
CAS No. 10247-90-2 1-Heptanaminium, N,N,N-triheptyl-, chloride (1:1) Catalog No.:AG0007KE MDL No.: MF:C28H60ClN MW:446.2357	CAS No. 10247-92-4 Stibine oxide, dihydroxy(4-nitrophenyl)- Catalog No.:AG0007KD MDL No.: MF:C6H6NO5Sb MW:293.8755	CAS No. 10247-98-0 Androst-5-en-3-one Catalog No.:AG0007KC MDL No.: MF:C19H28O MW:272.4250
CAS No. 102471-92-1 1-Propanone, 1,3-bis(2,4,6-trimethylphenyl)- Catalog No.:AG0007K7 MDL No.: MF:C21H26O MW:294.4305	CAS No. 1024724-31-9 3H-Pyrazol-3-one, 2,4-dihydro-5-methyl-4-[[5-nitro-2-(2-pyridinylthio)phenyl]methylene]-2-phenyl- Catalog No.:AG0007JR MDL No.:MFCD00955195 MF:C22H16N4O3S MW:416.4524	CAS No. 102476-22-2 Acetic acid, diphenyl-, 2-(1-ethyl-2-pyrrolidinyl)ethyl ester (6CI) Catalog No.:AG0007K6 MDL No.: MF:C22H27NO2 MW:337.4553
CAS No. 102478-64-8 9H-Fluoren-9-amine, N-methyl-N-(phenylmethyl)- Catalog No.:AG0007K5 MDL No.: MF:C21H19N MW:285.3823	CAS No. 102479-77-6 Phosphoramidazidimidic chloride (9CI) Catalog No.:AG0007K4 MDL No.: MF:ClH3N5P MW:139.4841	CAS No. 102479-78-7 Phosphoramidazidous chloride (9CI) Catalog No.:AG0007K3 MDL No.: MF:ClH2N4P MW:124.4694
CAS No. 102479-79-8 Phosphoramidous diazide (9CI) Catalog No.:AG0007K2 MDL No.: MF:H2N7P MW:131.0365	CAS No. 102479-80-1 Sulfamoyl iodide (9CI) Catalog No.:AG0007K1 MDL No.: MF:H2INO2S MW:206.9908	CAS No. 10248-82-5 1-Penten-1-one Catalog No.:AG0007KB MDL No.: MF:C5H8O MW:84.1164
CAS No. 10248-88-1 Thiourea, N'-(3,4-dichlorophenyl)-N,N-dimethyl- Catalog No.:AG0007KA MDL No.: MF:C9H10Cl2N2S MW:249.1601	CAS No. 102488-04-0 2-Octanone, 7-hydroxy-3,3-dimethyl- Catalog No.:AG0007JZ MDL No.: MF:C10H20O2 MW:172.2646	CAS No. 102488-47-1 Silane, chlorodimethyl(3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooctyl)- Catalog No.:AG0007JY MDL No.:MFCD00042359 MF:C10H10ClF13Si MW:440.7041
CAS No. 102488-49-3 Silane, trichloro(3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,11,11,12,12,12-heneicosafluorododecyl)- Catalog No.:AG0007JX MDL No.: MF:C12H4Cl3F21Si MW:681.5711	CAS No. 102488-50-6 Silane, trichloro(3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,11,11,12,12,13,13,14,14,14-pentacosafluorotetradecyl)- Catalog No.:AG0007JW MDL No.: MF:C14H4Cl3F25Si MW:781.5861	CAS No. 102488-79-9 3,5-Tetradecadien-1-ol, (3Z,5E)- Catalog No.:AG0007JV MDL No.: MF:C14H26O MW:210.3556
CAS No. 102488-95-9 Benzene, 1,1'-[(3-methylbutylidene)bis(thio)]bis- Catalog No.:AG0007JU MDL No.: MF:C17H20S2 MW:288.4707	CAS No. 102489-44-1 Ethanone, 1-[4-(3,6-dihydro-4-phenyl-1(2H)-pyridinyl)phenyl]- Catalog No.:AG0007JT MDL No.: MF:C19H19NO MW:277.3603	CAS No. 102489-51-0 Acetamide, N-(2-chloro-6-methylphenyl)-2-[[2-(diethylamino)ethyl](1-methylethyl)amino]-, hydrochloride (1:1) Catalog No.:AG0007JS MDL No.: MF:C18H31Cl2N3O MW:376.3642
CAS No. 102489-54-3 Acetamide, N-(2-chloro-6-methylphenyl)-2-[[2-(diethylamino)ethyl](2-phenoxyethyl)amino]-, hydrochloride (1:1) Catalog No.:AG0007KX MDL No.: MF:C23H33Cl2N3O2 MW:454.4330	CAS No. 102489-61-2 Acetamide, 2-[[2-(diethylamino)ethyl]thio]-N-(2-methylphenyl)-, hydrochloride (1:1) Catalog No.:AG0007KW MDL No.: MF:C15H25ClN2OS MW:316.8898	CAS No. 102489-71-4 L-Methionine, N-[[(2-chloroethyl)nitrosoamino]carbonyl]-, methyl ester Catalog No.:AG0007KV MDL No.: MF:C9H16ClN3O4S MW:297.7590
CAS No. 10249-10-2 Propanoic acid, 2,3,3,3-tetrafluoro-2-phenoxy-, phenyl ester Catalog No.:AG0007L0 MDL No.: MF:C15H10F4O3 MW:314.2317	CAS No. 10249-36-2 4(1H)-Pyridinone, 3-methyl- Catalog No.:AG0007KZ MDL No.:MFCD04114239 MF:C6H7NO MW:109.1259	CAS No. 10249-85-1 Sulfuric acid, bis(tributylstannyl) ester Catalog No.:AG0007KY MDL No.: MF:C24H54O4SSn2 MW:676.1502
CAS No. 102490-11-9 Ethanone, 1-[(2R,3S)-3-pentyl-2-oxiranyl]- Catalog No.:AG0007KU MDL No.: MF:C9H16O2 MW:156.2221	CAS No. 102490-65-3 4H-1-Benzopyran-4-one, 2-(2,4-dihydroxyphenyl)-2,3-dihydro-3,7-dihydroxy-5-methoxy-8-[(2R)-5-methyl-2-(1-methylethenyl)-4-hexen-1-yl]-, (2R,3S)- Catalog No.:AG0007KT MDL No.: MF:C26H30O7 MW:454.5122	CAS No. 102491-70-3 Acetamide, 2,2,2-trifluoro-N-(5,6,7,9-tetrahydro-10-hydroxy-1,2,3-trimethoxy-9-oxobenzo[a]heptalen-7-yl)- Catalog No.:AG0007KS MDL No.: MF:C21H20F3NO6 MW:439.3818
CAS No. 102491-80-5 Acetamide, N-(5,6,7,9-tetrahydro-2-hydroxy-1,3,10-trimethoxy-9-oxobenzo[a]heptalen-7-yl)- Catalog No.:AG0007KR MDL No.: MF:C21H23NO6 MW:385.4104	CAS No. 102492-19-3 Card-20(22)-enolide, 3-(β-D-glucopyranosyloxy)-, (3β,5β)- (9CI) Catalog No.:AG0007KQ MDL No.: MF:C29H44O8 MW:520.6549	CAS No. 102493-19-6 Fluoranthene, 2,4-dinitro- Catalog No.:AG0007KP MDL No.: MF:C16H8N2O4 MW:292.2457
CAS No. 102493-20-9 Fluoranthene, 1,2,4-trinitro- Catalog No.:AG0007KO MDL No.: MF:C16H7N3O6 MW:337.2433	CAS No. 102493-21-0 Fluoranthene, 2,5-dinitro- Catalog No.:AG0007KN MDL No.: MF:C16H8N2O4 MW:292.2457	CAS No. 102493-22-1 Fluoranthene, 1,2,5-trinitro- Catalog No.:AG0007KM MDL No.: MF:C16H7N3O6 MW:337.2433
CAS No. 102493-28-7 Lithium, [bis(dimethylphosphino)(trimethylsilyl)methyl]- Catalog No.:AG0007KL MDL No.: MF:C8H21LiP2Si MW:214.2264	CAS No. 102493-68-5 Benzeneethanol, 2-chloro-6-nitro- Catalog No.:AG0007KK MDL No.:MFCD00239018 MF:C8H8ClNO3 MW:201.6070	CAS No. 102494-22-4 Ethanone, 1-[4-(2-hydroxyethyl)phenyl]-, oxime Catalog No.:AG0007KJ MDL No.: MF:C10H13NO2 MW:179.2157
CAS No. 102494-28-0 5-Heptenoic acid, 7-[5-oxo-3-[(triethylsilyl)oxy]-1-cyclopenten-1-yl]-, methyl ester, (5Z)- Catalog No.:AG0007KI MDL No.:MFCD23135388 MF:C19H32O4Si MW:352.5405	CAS No. 102495-05-6 Pyridine, 4-(1-methyl-2-imidazolidinyl)- Catalog No.:AG0007KH MDL No.: MF:C9H13N3 MW:163.2196	CAS No. 102496-83-3 3-Pentenethioic acid, 4-methyl-, S-phenyl ester Catalog No.:AG0007KG MDL No.: MF:C12H14OS MW:206.3040
CAS No. 1025-12-3 2H-Cyclohepta[b]furan-3-carboxylic acid, 8-methoxy-2-oxo-, ethyl ester Catalog No.:AG0007L3 MDL No.: MF:C13H12O5 MW:248.2314	CAS No. 1025-22-5 Quinoxaline, 2-hydrazinyl-3-phenyl- Catalog No.:AG0007L2 MDL No.: MF:C14H12N4 MW:236.2719	CAS No. 1025-36-1 1,3-Diazetidine-2,4-dione, 1,3-diphenyl- Catalog No.:AG0007L1 MDL No.:MFCD00030165 MF:C14H10N2O2 MW:238.2414
CAS No. 10250-63-2 1H-Pyrazole-5-carboxylic acid, 1-methyl-3-phenyl-, ethyl ester Catalog No.:AG0007LD MDL No.:MFCD03933288 MF:C13H14N2O2 MW:230.2625	CAS No. 10250-64-3 1H-Pyrazole-5-carboxylic acid, 1-methyl-3-phenyl- Catalog No.:AG0007LC MDL No.:MFCD08271939 MF:C11H10N2O2 MW:202.2093	CAS No. 10250-66-5 β-Alanine, N-[(phenylamino)carbonyl]- Catalog No.:AG0007LB MDL No.:MFCD00099344 MF:C10H12N2O3 MW:208.2139
CAS No. 10250-67-6 Alanine, N-(2,4-dinitrophenyl)- Catalog No.:AG0007LA MDL No.: MF:C9H9N3O6 MW:255.1843	CAS No. 10250-82-5 Ethanaminium, 2-bromo-N,N,N-trimethyl- Catalog No.:AG0007L9 MDL No.: MF:C5H13BrN+ MW:167.0674	CAS No. 1025010-58-5 Boronic acid, B-(8-methyl-5-quinolinyl)- Catalog No.:AG0007L6 MDL No.:MFCD05256435 MF:C10H10BNO2 MW:187.0029
CAS No. 102502-64-7 Tricyclo[3.3.1.13,7]decane-1-acetic acid, α-amino-, hydrochloride (1:1), (αS)- Catalog No.:AG0007L8 MDL No.: MF:C12H20ClNO2 MW:245.7457	CAS No. 102502-67-0 4-Octanone, 1,2-dichloro- Catalog No.:AG0007L7 MDL No.: MF:C8H14Cl2O MW:197.1022	CAS No. 1025023-04-4 Hasubanan-6-one, 8,10-epoxy-7,8-dimethoxy-17-methyl-2,3-[methylenebis(oxy)]-, (7α,8β,10β)- Catalog No.:AG0007L5 MDL No.:MFCD20274975 MF: MW: