1-(Phenylsulfonyl)-1H-indole → 4-(1-benzenesulfonyl-1H-indol-2-yl)-4-hydroxy4H-naphthalen-1-one

HRID 969609Notes

Reaction equation

HRID 969609 reaction equation
CO[C:3]1([O:14]C)[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6](=[O:13])[CH:5]=[CH:4]1.[C:16]1([S:22]([N:25]2[C:33]3[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=3)[CH:27]=[CH:26]2)(=[O:24])=[O:23])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>>[C:16]1([S:22]([N:25]2[C:33]3[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=3)[CH:27]=[C:26]2[C:3]2([OH:14])[C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[C:6](=[O:13])[CH:5]=[CH:4]2)(=[O:24])=[O:23])[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1

Participants

3

Reactant 2

HCID 3150171-(Phenylsulfonyl)-1H-indoleHCID 110957174,4-dimethoxy-4H-naphthalen-1-one

Product 1

HCID 102512744-(1-benzenesulfonyl-1H-indol-2-yl)-4-hydroxy4H-naphthalen-1-oneYield 20%

Procedure

The title compound was prepared from 4,4-dimethoxy-4H-naphthalen-1-one and 1-benzenesulfonyl-1H-indole, according to Method E, described above. Yield 20%; mp 175-177° C.; 1H NMR (CDCl3) δ 8.19-8.23 (dd, J=7 Hz, 1H), 8.02-8.05 (dd, J=9 Hz, 1H), 7.80-7.92 (m, 4H), 7.68-7.73 (t, J=7 Hz, 1H), 7.55-7.64 (m, 2H), 7.42-7.48 (t, J=7 Hz, 2H), 7.25-7.32 (m, 3H), 7.14-7.20 (m, 1H), 6.37 (d, J=11 Hz, 1H); 13C NMR (CDCl3) δ 189.7, 153.9, 149.7, 148.9, 143.7, 143.2, 139.0, 137.9, 135.7, 134.2, 133.7, 133.6, 132.4, 131.6, 131.3, 130.8, 129.4, 126.7, 120.5, 74.9; MS (AP+) m/z 416.07 (M++1), 398.06.

Sources & evidence

ORD record
ord-2193cc5246774becbe12a292c01e6df7
Source dataset
uspto-grants-2007_12
Patent number
US07307099B2

Reaction notes

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