1-(Phenylsulfonyl)-1H-indole → 4-Hydroxy-4-[1-(phenylsulfonyl)-1H-indol-2-yl]-2,5-cyclohexadien-1-one

HRID 969605Notes

Reaction equation

HRID 969605 reaction equation
CO[C:3]1([O:10]C)[CH:8]=[CH:7][C:6](=[O:9])[CH:5]=[CH:4]1.[C:12]1([S:18]([N:21]2[C:29]3[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=3)[CH:23]=[CH:22]2)(=[O:20])=[O:19])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>>[C:12]1([S:18]([N:21]2[C:29]3[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=3)[CH:23]=[C:22]2[C:3]2([OH:10])[CH:4]=[CH:5][C:6](=[O:9])[CH:7]=[CH:8]2)(=[O:20])=[O:19])[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

3

Reactant 2

HCID 3150171-(Phenylsulfonyl)-1H-indoleHCID 3946484,4-Dimethoxy-2,5-cyclohexadien-1-one

Product 1

HCID 99071344-Hydroxy-4-[1-(phenylsulfonyl)-1H-indol-2-yl]-2,5-cyclohexadien-1-oneYield 18%

Procedure

The title compound was prepared from 4,4-dimethoxy-cyclohexa-2,5-dienone and 1-benzenesulfonyl-1H-indole (available commercially), according to Method C, described above. Yield 18%; mp 170-172° C.; 1H NMR (CDCl3) δ 8.0 (d, J=8 Hz, 1H), 7.87 (d, J=8 Hz, 2H), 7.51-7.60 (m, 3H), 7.30-7.46 (m, 3H), 7.18-7.27 (m, 2H), 6.80 (s, 1H), 6.32 (d, J=10 Hz, 2H), 5.50 (s, 1H); 13C NMR (CDCl3) δ 185.3, 147.9, 141.2, 138.6, 137.8, 134.7, 129.7, 128.7, 128.1, 127.0, 126.6, 125.0, 122.1, 115.6, 114.1, 67.9.

Sources & evidence

ORD record
ord-3dff662cbd504f2bbec6cc1bd138fd9c
Source dataset
uspto-grants-2007_12
Patent number
US07307099B2

Reaction notes

Loading…