4,4-Dimethoxy-2,5-cyclohexadien-1-one → HCID 10430793, compound

HRID 969606Notes

Reaction equation

HRID 969606 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][C:26]([O:30][CH3:31])=[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][C:26]([O:30][CH3:31])=[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:19])=[O:20])[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

3

Reactant 2

HCID 3946484,4-Dimethoxy-2,5-cyclohexadien-1-oneHCID 64736791-benzenesulfonyl-5-methoxy-1H-indole

Product 1

HCID 10430793HCID 10430793, compoundYield 32%

Procedure

The title compound was prepared from 4,4-dimethoxy-cyclohexa-2,5-dienone and 1-benzenesulfonyl-5-methoxy-1H-indole, according to Method C, described above. Yield 32%; mp 126-128° C.; 1H NMR (CDCl3) δ 7.73-7.83 (m, 3H), 7.40-7.49 (m, 2H), 7.33-7.40 (m, 2H), 6.76-6.84 (m, 3H), 6.64 (s, 1H), 6.20 (d, J=10 Hz, 2H), 5.40 (s, 1H), 3.67 (s, 3H); 13C NMR (CDCl3) δ 196.6, 185.3, 157.3, 147.9, 141.8, 137.7, 134.3, 133.2, 129.8, 129.7, 129.3, 127.9, 126.9, 116.8, 115.4, 114.4, 104.2, 81.2, 67.9, 55.9; MS (AP+) m/z 396.09 (M++1), 378.08.

Sources & evidence

ORD record
ord-83fd6174b58245cd9d53d1facfda4e37
Source dataset
uspto-grants-2007_12
Patent number
US07307099B2

Reaction notes

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