Potassium Carbonate → HCID 44816051, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 300 mg (0.789 mmol) of N-(2-bromobenzyl)-N-cyclopropyl-5-fluoro-1,3-dimethyl-1H-pyrazole-4-carboxamide in 10 ml of tetrahydrofurane are successively added 120 mg (0.986 mmol) of phenylboronic acid, 163 mg (1.183 mmol) of potassium carbonate dissolved in 5 ml of water and 9 mg (0.01 equivalent) of tetrakis(triphenylphosphine)palladium. The reaction mixture is heated at 80° C. for 4 hrs. The reaction mixture is then cooled to ambient temperature and poured on 50 ml of brine. The watery layer is extracted three times with diethyl ether and the combined organic layers are successively washed by a 1M solution of sodium hydroxide, brine and filtered over a phase separator filter to yield after concentration 310 mg of a brown oil. Column chromatography (gradient heptane/ethyl acetate) yielded 220 mg (68% yield) of N-[1-(biphenyl-2-yl)ethyl]-N-cyclopropyl-5-fluoro-1,3-dimethyl-1H-pyrazole-4-carboxamide as a white solid; melting point [mp]=100° C.

Provenance & Evidence