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

Participants

Reaction Steps

A solution of acid 4A (260 mg, 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-(trifluoromethyl)phenyl]-4-pyridyl]methanamine 21A (1.1 equiv., 277.5 mg) was 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 anhydrification over Na2SO4, was evaporated under reduced pressure and the residue was purified by flash chromatography (1:1 EtOAc:Petroleum ether) to afford a pale yellow solid (100 mg) after crystallization from a mixture of diethyl ether/petroleum ether. Yield=49%, 1HNMR (DMSO, 400 MHz) δ 2.93 (3H, s), 4.48 (d, 2H, J=6 Hz), 5.08 (s, 1H), 5.87 (s, 1H), 7.35 (d, 1H), 7.37 (t, 2H, J=8.8 Hz), 7.82 (m, 4H), 8.03 (s, 1H), 8.28 (d, 2H, J=8.4 Hz), 8.63 (d, 1H, J=5.2 Hz), 8.95 (bt, 1H); [M+1] 494.47 (C23H19F4N3O3S requires 493.47).

Provenance & Evidence