Sodium hydride → N-(3-chloro-2-ethylpyridin-4-yl)-N-methoxycarbonyl-4-[(5-trifluoromethylpyridin-2-yl)oxy]phenylacetamide

Participants

Reaction Steps

2.0 g (9.3 mmol) of methyl N-(3-chloro-2-ethylpyridin-4-yl)-carbamate was dissolved in 10 ml of N,N-dimethylacetamide, and the solution was stirred at room temperature. Then, 0.27 g (11.2 mmol) of sodium hydride was gradually added thereto, and the mixture was stirred for one hour at room temperature. Then, 5.5 g (17.4 mmol) of 4-[(5-trifluoromethylpyridin-2-yl)oxy]phenylacetyl chloride was dropwise added thereto at -15° C., and the mixture was stirred for 3 hours at a temperature of from -15° to -10° C. Then, the reaction solution was poured into a sodium hydrogen carbonate solution cooled with ice and extracted with ethyl acetate. The organic layer was washed with water and then dried over anhydrous magnesium sulfate. Then, ethyl acetate was distilled off under reduced pressure. The obtained residue was purified by silica gel column chromatography (developing solvent: n-hexane/ethyl acetate) and further purified by a thin layer chromatography to obtain 1.2 g of the desired product as a white powder (melting point: 62° to 64° C.).

Provenance & Evidence