Benzenesulfonyl chloride → 1h-Indole-2-carboxylic acid,1-[[4-[(phenylsulfonyl)amino]phenyl]methyl]-3-(2-thienyl)-

HRID 916197Notes

Reaction equation

HRID 916197 reaction equation
C([O:3][C:4]([C:6]1[N:7]([CH2:20][C:21]2[CH:26]=[CH:25][C:24]([NH2:27])=[CH:23][CH:22]=2)[C:8]2[C:13]([C:14]=1[C:15]1[S:16][CH:17]=[CH:18][CH:19]=1)=[CH:12][CH:11]=[CH:10][CH:9]=2)=[O:5])C.[C:28]1([S:34](Cl)(=[O:36])=[O:35])[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1>>[C:28]1([S:34]([NH:27][C:24]2[CH:25]=[CH:26][C:21]([CH2:20][N:7]3[C:8]4[C:13](=[CH:12][CH:11]=[CH:10][CH:9]=4)[C:14]([C:15]4[S:16][CH:17]=[CH:18][CH:19]=4)=[C:6]3[C:4]([OH:3])=[O:5])=[CH:22][CH:23]=2)(=[O:36])=[O:35])[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1

Participants

3

Reactant 2

HCID 7369Benzenesulfonyl chlorideHCID 694339351h-Indole-2-carboxylic acid,1-[(4-aminophenyl)methyl]-3-(2-thienyl)-,ethyl ester

Product 1

HCID 112139591h-Indole-2-carboxylic acid,1-[[4-[(phenylsulfonyl)amino]phenyl]methyl]-3-(2-thienyl)-

Procedure

The title compound was prepared from 1-(4-amino-benzyl)-3-thiophene-2-yl-1H-indole-2-carboxylic acid ethyl ester and benzenesulfonyl chloride followed the procedure of Example 3 Step 2 as a light brown solid: 1H NMR (DMSO-d6) δ 5.67 (s, 2H), 6.95-7.05 (m, 4H), 7.14-7.23 (m, 3H), 7.30-7.35 (m, 1H), 7.49-7.75 (m, 8H), 10.26 (br s, 1H), 13.24 (br s, 1H); MS (ESI) m/z 489 (MH+); HRMS calcd for C26H21N2O4S2: 489.0940; found (ESI+): 489.0935.

Sources & evidence

ORD record
ord-82214e0962654922b62be05604a982df
Source dataset
uspto-grants-2007_09
Patent number
US07268159B2

Reaction notes

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