[C:1]([C:3]1[CH:22]=[CH:21][C:6]([C:7]([N:9]([CH3:20])[C:10]2[CH:15]=[CH:14][C:13]([C:16]([F:19])([F:18])[F:17])=[CH:12][CH:11]=2)=[O:8])=[CH:5][C:4]=1[CH3:23])#[N:2].[BH4-].[Na+].[NH4+].[Cl-]>CO.O.O.O.O.O.O.[Co](Cl)Cl>[NH2:2][CH2:1][C:3]1[CH:22]=[CH:21][C:6]([C:7]([N:9]([CH3:20])[C:10]2[CH:11]=[CH:12][C:13]([C:16]([F:17])([F:18])[F:19])=[CH:14][CH:15]=2)=[O:8])=[CH:5][C:4]=1[CH3:23]
A solution of 4-cyano-3,N-dimethyl-N-(4-trifluoromethyl-phenyl)-benzamide from Example E118.2 (1.08 g, 3.4 mmol) in methanol (40 ml) at room temperature was treated with cobalt(II) chloride hexahydrate (1.61 g, 6.8 mmol). The mixture was stirred for 10 min then sodium borohydride (1.28 g, 34 mmol) was added portionwise. The mixture was stirred for 20 h then saturated NH4Cl solution (10 ml) was added. The mixture was stirred for 30 min, filtered through glass-fibre paper and the filtrate was concentrated in vacuo. The residue was purified by flash chromatography on silica gel (eluant; 1% 35% ammonia:9% methanol:90% dichloro-methane) to yield the title compound (863 mg, 79%).
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