[NH2:1][C:2]1[C:10]2[N:9]=[CH:8][N:7]([C:11]3[CH:18]=[CH:17][C:14]([C:15]#[N:16])=[CH:13][CH:12]=3)[C:6]=2[CH:5]=[CH:4][CH:3]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[CH:33](=O)[CH:34]([CH3:36])[CH3:35].C(O)(=O)C>ClCCl>[CH3:33][CH:34]([CH3:36])[CH2:35][NH:1][C:2]1[C:10]2[N:9]=[CH:8][N:7]([C:11]3[CH:18]=[CH:17][C:14]([C:15]#[N:16])=[CH:13][CH:12]=3)[C:6]=2[CH:5]=[CH:4][CH:3]=1To a stirred solution of 4-(4-amino-1H-benzimidazol-1-yl)benzonitrile (246 mg, 1.05 mmol) in dichloromethane (10 mL) at rt was added sodium triacetoxy borohydride (311 mg, 1.47 mmol, 1.4 eq), isobutyraldehyde (91 mg, 1.26 mmol, 1.2 eq) and acetic acid (63 m g, 1.05 mmol, 1 eq) and the mixture was stirred for 2 h. The mixture was poured on water and extracted with DCM. After evaporation of the organic phase, purification of the residue by flash chromatography yielded 190 mg 4-{4-[(2-methylpropyl)amino]-1H-benzimidazol-1-yl}benzonitrile (62.3%).
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