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

HRID 916192Notes

Reaction equation

C([O:3][C:4](C1NC2C(C=1)=CC=CC=2)=[O:5])C.[NH2:15][C:16]1[CH:37]=[CH:36][C:19]([CH2:20][N:21]2[C:29]3[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=3)[C:23]([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)=[CH:22]2)=[CH:18][CH:17]=1.[C:38]1([S:44](Cl)(=[O:46])=[O:45])[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1>>[C:30]1([C:23]2[C:24]3[C:29](=[CH:28][CH:27]=[CH:26][CH:25]=3)[N:21]([CH2:20][C:19]3[CH:18]=[CH:17][C:16]([NH:15][S:44]([C:38]4[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=4)(=[O:46])=[O:45])=[CH:37][CH:36]=3)[C:22]=2[C:4]([OH:5])=[O:3])[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=1

Participants

Reactant 2

HCID 7369Benzenesulfonyl chloride

HCID 694354711-(4-Amino-benzyl)-3-phenyl-1H-indole indolecarboxylic acid ethyl ester

Product 1

HCID 113176571h-Indole-2-carboxylic acid,3-phenyl-1-[[4-[(phenylsulfonyl)amino]phenyl]methyl]-

Procedure

The title compound was prepared from 1-(4-amino-benzyl)-3-phenyl-1H-indole indolecarboxylic acid ethyl ester and benzenesulfonyl chloride followed the procedure of Example 3 Step 2 as an off-white solid: 1H NMR (DMSO-d6) δ 5.72 (s, 2H), 6.95-7.00 (m, 4H), 7.09-7.13 (m, 1H), 7.27-7.31 (m, 1H), 7.33-7.37 (m, 1H), 7.42-7.45 (m, 5H), 7.49-7.55 (m, 3H), 7.57-7.61 (m, 1H), 7.72 (dd, J=7.1, 1.4 Hz, 2H), 10.26 (br s, 1H), 12.83 (br s, 1H); MS (ESI) m/z 481 ([M−H]−); HRMS calcd for C28H21N2O4S: 481.1224; found (ESI−): 481.1228.

Sources & evidence

ORD record: ord-f53bfaf9908840318d21eae85435b61b
Source dataset: uspto-grants-2007_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07268159B2

Reaction notes

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