General procedure for the synthesis of 5-trifluoromethylpyridine-3-methanamine from 2-chloro-5-(trifluoromethyl)nicotinonitrile: Nickel Nguyenay (300 mg) was added to a mixture of ethanol (40 ml) and ammonium hydroxide (5 ml) of the product of step D (1 g, 4.9 mmol). The reaction mixture was subjected to hydrogenation at 40°C with hydrogen pressure kept constant and the reaction lasted for 7 hours. After completion of the reaction, the catalyst was removed by filtration and the filtrate was concentrated under vacuum. The residue was purified by medium pressure liquid chromatography (MPLC, Biotage Flash 40 system) using a CH2Cl2 solution of 2% CH3OH containing 0.5% NH4OH as eluent, resulting in the target product 5-trifluoromethylpyridine-3-methylamine (250 mg, 30% yield). The structure of the product was confirmed by 1H NMR (500 MHz, CDCl3): δ = 4.00 (2H, s), 7.95 (1H, s), 8.75 (2H, d, J = 5.26 Hz).
