4-t-Butylbenzenesulfonyl chloride → 5-{[(4-tert-butylphenyl)sulfonyl]amino}-1-methyl-3-phenyl-1H-indole-2-carboxylic Acid
Reaction equation
[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][C:7]([N+:11]([O-])=O)=[CH:8][CH:9]=2)[C:4]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[C:3]1[C:20]([O:22]CC)=[O:21].[C:25]([C:29]1[CH:34]=[CH:33][C:32]([S:35](Cl)(=[O:37])=[O:36])=[CH:31][CH:30]=1)([CH3:28])([CH3:27])[CH3:26]>>[C:25]([C:29]1[CH:34]=[CH:33][C:32]([S:35]([NH:11][C:7]2[CH:6]=[C:5]3[C:10](=[CH:9][CH:8]=2)[N:2]([CH3:1])[C:3]([C:20]([OH:22])=[O:21])=[C:4]3[C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)(=[O:37])=[O:36])=[CH:31][CH:30]=1)([CH3:28])([CH3:26])[CH3:27]Participants
3
Procedure
The title compound was prepared from ethyl 1-methyl-5-nitro-3-phenyl-1H-indole-2-carboxylate and 4-tert-butylbenzene sulfonyl chloride followed the procedures of Example 1 Step 2 & Step 3 as a pale yellow solid: 1H NMR (DMSO-d6) δ 1.25 (s, 9H, 3.94 (s, 3H, 7.00-7.10 (m, 1H, 7.10-7.27 (m, 3H, 7.27-7.45 (m, 3H, 7.45-7.62 (m, 5H, 9.86 (s, 1H), 12.97 (br s, 1H; MS (ESI) m/z 461 [M-H]−; HRMS calcd for C26H27N2O4S: 463.1689; found (ESI+): 463.1681; Anal. calcd for C26H26N2O4S.0.15H2O: C, 67.12; H, 5.70; N, 6.02. Found: C, 67.05; H, 5.42; N, 5.88.
Sources & evidence
- ORD record
- ord-2af0d434b5d547f6baeebd256c51d462
- Source dataset
- uspto-grants-2008_10
- Patent number
- US07442805B2
Reaction notes
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