N-(4-Cyano-2-fluorophenyl)methanesulfonamide → N-(4-(aminomethyl)-2-fluorophenyl)methanesulfonamide

Participants

Reaction Steps

A mixture of Example 10B (3.40 g, 16.0 mmol) and nickel powder (6.72 g, 114 mmol) in 7M NH3-MeOH (40 mL) in a 250 mL stainless steel pressure bottle at room temperature was stirred at 30 psi for 6 hours. The mixture was filtered through a nylon membrane (MeOH and THF wash) and the filtrate concentrated to afford the title compound (3.5 g), which was used without further purification. 1H NMR (300 MHz, CD3OD) δ 7.43 (t, J=8.2 Hz, 1H), 7.19 (dd, J=11.5, 1.3 Hz, 1H), 7.13 (d, J=8.3 Hz, 1H), 3.81 (s, 2H), 2.96 (s, 3H); MS (ESI) m/z 219 (M+H+).

Provenance & Evidence