[CH:1]1[CH:2]=[CH:3][N:4]2[C:13]=1[C:12](=[O:14])[C:11]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[NH:5]2.C(=O)([O-])[O-].[K+].[K+].[CH2:21](Br)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>CC(=O)CC>[CH2:21]([N:5]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:11]=2[C:12](=[O:14])[C:13]2=[CH:1][CH:2]=[CH:3][N:4]12)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1A stirred slurry containing pyrrolo[1,2-b]cinnolin-10(5H)-one (4.0 g) and potassium carbonate (11.2 g) in 100 ml of 2-butanone was treated with benzyl bromide (4.0 g) and the mixture was stirred at 60°. After 4 h the mixture was quenched with 700 ml of H2O and extracted with two 150 ml portions of dichloromethane. These organic extracts were dried over MgSO4, filtered and concentrated to a green oil. This oil was purified by flash chromatography (silica, dichloromethane) to a yellow solid which was recrystallized from dichloromethane to give 3.5 g of bright yellow crystals, mp 146°-148°.
Loading…
