[Br:1][C:2]1[CH:3]=[C:4]([CH2:9][CH2:10][C:11]#[N:12])[CH:5]=[CH:6][C:7]=1[F:8].CO.C([Cl:18])(=O)C.[NH3:19]>C1(C)C=CC=CC=1>[ClH:18].[Br:1][C:2]1[CH:3]=[C:4]([CH2:9][CH2:10][C:11](=[NH:19])[NH2:12])[CH:5]=[CH:6][C:7]=1[F:8]
To a solution of 3-(3-bromo-4-fluorophenyl)propanenitrile (5.0 g, 21.05 mmol) in toluene (20 mL) and methanol (6.32 mL, 156 mmol) at 0° C. was added acetyl chloride (7.51 mL, 105 mmol) dropwise over 5 min. The reaction mixture was allowed to warm to room temperature and stirred for 2 h. The mixture was cooled to 0° C. by an ice bath, to which ammonia (30.1 mL, 210 mmol) was added dropwise. The reaction mixture was stirred at room temperature overnight. The mixture was filtered, and the filtrate was concentrated to give a crude product. Recrystallization from toluene/methanol (1:1) then afforded the title compound as a white solid (5.2 g, 93% yield). LCMS: rt=1.18 min, [M+H+]=245
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