Diethyl Pyrocarbonate → 2-[(4-fluorophenyl)sulfonyl-methyl-amino]-N-[[2-[4-(trifluoromethoxy)phenyl]-4-pyridyl]methyl]prop-2-enamide

Participants

Reaction Steps

A solution of acid 4A (0.26 g, 1 mmol) in THF (25 mL) was added with DEPC (0.18 mL, 1.3 mol eq) and the mixture was stirred at room temperature for about 5 minutes. Then [2-[4-(trifluoromethoxy)phenyl]-4-pyridyl]methanamine 21B (0.27 g, 1.1 mol eq) and a catalytic amount of TEA were added. The reaction mixture was then stirred at room temperature overnight. The solvent was removed under reduced pressure, the residue was suspended in EtOAc (30 mL) and washed with water (50 mL) and brine. The separated organic phase, after drying over Na2SO4, was evaporated under reduced pressure and the residue was purified by flash chromatography (8:2 EtOAc:Petroleum ether) to afford a pale yellow solid (0.1 g) after crystallization from a mixture of diethyl ether/petroleum ether. Yield=23%, 1HNMR (DMSO, 200 MHz) δ 2.95 (3H, s), 4.49 (d, 2H, J=6 Hz), 5.10 (s, 1H), 5.88 (s, 1H), 7.35 (dd, 1H), 7.47 (m, 4H), 7.48 (m, 2H), 7.96 (s, 1H), 8.21 (dd, 2H), 8.61 (d, 1H, J=4 Hz), 8.94 (t, 1H); [M+1] 509.47 (C23H19F4N3O4S requires 509.10).

Provenance & Evidence