[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:12])=[C:6]([CH:11]=1)[C:7]([NH:9][CH3:10])=[O:8].C([N-]C(C)C)(C)C.[Li+].[F:21][C:22]1[CH:29]=[CH:28][C:25](C#N)=[CH:24][C:23]=1[O:30][CH3:31].[NH4+].[Cl-]>C1COCC1>[Cl:1][C:2]1[CH:11]=[C:6]2[C:5]([CH:12]=[C:10]([C:25]3[CH:28]=[CH:29][C:22]([F:21])=[C:23]([O:30][CH3:31])[CH:24]=3)[NH:9][C:7]2=[O:8])=[CH:4][CH:3]=1A solution of 5-chloro-2,N-dimethylbenzamide (5.0 g, 27.2 mmol) in THF (28 mL) was cooled to −78° C. and a solution of 2M lithium diisopropylamide in THF (40.8 mL, 82 mmol) diluted with THF (68 mL) added. 4-Fluoro-3-methoxybenzonitrile (4.12 g, 27.2 mmol) in THF (28 mL) was added and the mixture stirred at −78° C. for 2.5 h. Sat. NH4Cl (aq.) was added and the mixture extracted with EtOAc (2×50 mL). A precipitate formed in the aqueous which was collected by filtration to afford 7-chloro-3-(4-fluoro-3-methoxyphenyl)-2H-isoquinolin-1-one (3.74 g, 12.3 mmol, 45%).
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