[BH4-].[Na+].[C:3]([C:11]1[CH:16]=[CH:15][C:14]([C:17]2[CH:24]=[N:23][CH:22]=[C:21]([Cl:25])[C:18]=2[C:19]#[N:20])=[CH:13][CH:12]=1)(=[O:10])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1>ClCCl.CO>[Cl:25][C:21]1[CH:22]=[N:23][CH:24]=[C:17]([C:14]2[CH:13]=[CH:12][C:11]([CH:3]([OH:10])[C:4]3[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=3)=[CH:16][CH:15]=2)[C:18]=1[C:19]#[N:20]Granular sodium borohydride (225 mg, 5.94 mmol) was added to a solution of 3-(4-benzoylphenyl)-5-chloroisonicotinonitrile (473 mg, 1.187 mmol, 80% pure) in dichloromethane (10 mL) and methanol (10 mL). After 30 min at room temperature, the mixture was quenched with saturated ammonium chloride (30 mL). The organic solvents were evaporated in vacuo. The aqueous residue was extracted with ethyl acetate (2×40 mL). The combined extracts were washed with brine (5 mL), dried (MgSO4) and concentrated. Silica gel chromatography, loading with dichloromethane and eluting with 20-60% ethyl acetate in hexanes, gave 3-chloro-5-(4-(hydroxy(phenyl)methyl)phenyl)isonicotinonitrile as white solid (327 mg, 69% yield), which was approximately 80% pure. MS (ES+) m/z: 303 (M−water+H); LC retention time: 3.798 min (analytical HPLC Method A).
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