C([N-]C(C)C)(C)C.[Li+].[Br:9][C:10]1[CH:11]=[CH:12][C:13]([CH3:20])=[C:14]([CH:19]=1)[C:15]([NH:17][CH3:18])=[O:16].[Cl:21][C:22]1[CH:23]=[C:24]([CH:27]=[CH:28][CH:29]=1)C#N.[NH4+].[Cl-]>O1CCCC1>[Br:9][C:10]1[CH:19]=[C:14]2[C:13]([CH:20]=[C:18]([C:28]3[CH:27]=[CH:24][CH:23]=[C:22]([Cl:21])[CH:29]=3)[NH:17][C:15]2=[O:16])=[CH:12][CH:11]=1
To a solution of 2M lithium diisopropylamide (19.73 mL, 39.5 mmol) in tetrahydrofuran (30 mL) at −78° C. was added dropwise a solution of 5-bromo-N,2-dimethylbenzamide (Intermediate 22A) (3.0 g, 13.15 mmol) in THF (14 mL) followed by a solution of 3-chlorobenzonitrile (1.809 g, 13.15 mmol) in THF (14 mL) and the mixture was stirred at −78° C. for 2.5 hours. Reaction allowed to warm to room temperature and saturated NH4Cl (aq) was added. The THF was removed under reduced pressure and the resulting mixture extracted into ethyl acetate and washed with brine (precipitate was observed in both layers). Organics were evaporated to dryness, washed with methanol and dried in a vacuum oven to afford 7-bromo-3-(3-chlorophenyl)isoquinolin-1(2H)-one (0.9 g, 2.69 mmol).
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