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

Participants

Reaction Steps

A solution of acid 4B (0.25 g, 1 mmol) in THF (20 mL) was added with DEPC (0.17 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, then the reaction mixture was 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 purified by flash chromatography (7:3 EtOAc:Petroleum ether) to afford a pale orange solid (0.12 g) after crystallization from a mixture of diethyl ether/petroleum ether.

Provenance & Evidence