Propargyl bromide → HCID 19082073, compound

Participants

Reaction Steps

1.0 g (2.3 mmol) of N-(3-chloro-2-ethylpyridin-4-yl)-4-[(5-trifluoromethylpyridin-2-yl)oxy]phenylacetamide was dissolved in 5 ml of N,N-dimethylacetamide, and the solution was stirred at room temperature. Then, 0.067 g (2.8 mmol) of sodium hydride was gradually added thereto, and the mixture was further stirred for one hour at room temperature. Then, 10.3 (2.5 mmol) of propargyl bromide was added thereto, and the mixture was stirred for one hour at room temperature. Then, 0.3 g (2.5 mmol) of propargyl bromide was further added thereto, and the mixture was stirred for one hour at a temperature of from 50° to 60° C. Then, the reaction solution was poured into ice water 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 then purified by high performance liquid chromatography to obtain 0.5 g of the desired product as a brown viscous substance (refractive index nD20 =1.35619).

Provenance & Evidence