Potassium tert-butoxide → 4-(3-bromophenyl)-6,7-dimethoxy-3-(thiophen-2-yl)quinolin-2(1H)-one
Reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:8]([C:10]2[CH:15]=[C:14]([O:16][CH3:17])[C:13]([O:18][CH3:19])=[CH:12][C:11]=2[NH:20][C:21](=[O:28])[CH2:22][C:23]2[S:24][CH:25]=[CH:26][CH:27]=2)=O)[CH:5]=[CH:6][CH:7]=1.CC([O-])(C)C.[K+]>C1COCC1>[Br:1][C:2]1[CH:3]=[C:4]([C:8]2[C:10]3[C:11](=[CH:12][C:13]([O:18][CH3:19])=[C:14]([O:16][CH3:17])[CH:15]=3)[NH:20][C:21](=[O:28])[C:22]=2[C:23]2[S:24][CH:25]=[CH:26][CH:27]=2)[CH:5]=[CH:6][CH:7]=1Participants
4
Procedure
To a solution of N-{2-[(3-bromophenyl)carbonyl]-4,5-dimethoxyphenyl}-2-(thiophen-2-yl)acetamide (8 g, 17.4 mmol) in dry THF (80 mL) was added t-BuOK (6 g 52.1 mmol) in portions at 0° C. The reaction mixture was stirred for 1 hour and concentrated under reduced pressure. The residue was diluted with EtOAc (50 mL). The combined organic layers were dried over anhydrous MgSO4, filtered and concentrated in vacuum to afford 4-(3-bromophenyl)-6,7-dimethoxy-3-(thiophen-2-yl)quinolin-2(1H)-one. MS (M+H)=442 and 444.