Potassium Carbonate → 1-(4-cyanonaphthalene-2-yl)-1H-pyrazole-3-carboxylic acid ethyl ester

Participants

Reaction Conditions

Reaction Steps

A suspension of 1H-pyrazole-3-carboxylic acid ethyl ester (0.1 g), 3-bromonaphthalene-1-carbonitrile (0.17 g), copper iodide (0.0068 g), (1R,2R)-(−)-N, N′-dimethylcyclohexane-1,2-diamine (0.010 g) and potassium carbonate (0.21 g) in toluene (3 mL) was stirred at 90° C. overnight. After cooling to room temperature, ethyl acetate was added to the reaction mixture. The resulting mixture was filtered through a Celite pad. The residue was purified by column chromatography on silica gel (eluent: n-hexane/ethyl acetate=100/0-66/34) to give 1-(4-cyanonaphthalene-2-yl)-1H-pyrazole-3-carboxylic acid ethyl ester (0.040 g). To a solution of this compound (0.040 g) in a mixed solvent of tetrahydrofuran (0.2 mL), ethanol (0.08 mL) and water (0.08 mL) was added lithium hydroxide monohydrate (0.017 g), and the mixture was stirred at room temperature overnight. To the reaction mixture was added 2 mol/L hydrochloric acid (0.35 mL). The precipitated solid was collected by filtration, washed with water and n-hexane, and dried under reduced pressure to give the title compound (0.026 g).

Provenance & Evidence