p-(Trifluoromethoxy)benzenesulphonyl chloride → 1-methyl-3-phenyl-5-({[4-(trifluoromethoxy)phenyl]sulfonyl}amino)-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].[F:25][C:26]([F:39])([F:38])[O:27][C:28]1[CH:33]=[CH:32][C:31]([S:34](Cl)(=[O:36])=[O:35])=[CH:30][CH:29]=1>>[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][C:7]([NH:11][S:34]([C:31]3[CH:30]=[CH:29][C:28]([O:27][C:26]([F:25])([F:38])[F:39])=[CH:33][CH:32]=3)(=[O:36])=[O:35])=[CH:8][CH:9]=2)[C:4]([C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)=[C:3]1[C:20]([OH:22])=[O:21]Participants
3
Procedure
The title compound was prepared from ethyl 1-methyl-5-nitro-3-phenyl-1H-indole-2-carboxylate and 4-trifluoromethoxy-benzenesulfonyl chloride followed the procedures of Example 1 Step 2 & Step 3 as an off-white solid: 1H NMR (DMSO-d6) δ 3.95 (s, 3H), 6.98 (d, J=2.8 Hz, 1H, 7.11 (dd, J=8.8, 1.7 Hz, 1H, 7.21 (d, J=8.0 Hz, 2H, 7.30-7.45 (m, 3H, 7.50-7.60 (m, 3H, 7.74 (d, J=8.7 Hz, 2H, 9.98 (s, 1H, 13.00 (br s, 1H; MS (ESI) m/z 489[M-H]−; HRMS calcd for C23H18F3N2O5S: 491.0886; found (ESI+): 491.0878; Anal. calcd for C23H17F3N2O5S.0.4H2O: C, 55.51; H, 3.61; N, 5.63. Found: C, 55.61; H, 3.39; N, 5.77.
Sources & evidence
- ORD record
- ord-7aae4dbdf52340f783b563de7b10c864
- Source dataset
- uspto-grants-2008_10
- Patent number
- US07442805B2
Reaction notes
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