Diethyl Ether → HCID 22120916, compound

Participants

Reaction Steps

To a rapidly stirred solution of 5-amino-3-cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)-4-iodopyrazole (1 g) in toluene (6 ml) containing tetrakis(triphenylphosphine)palladium(0) (0.05 g) was added saturated aqueous sodium hydrogen carbonate solution (3 ml) and a solution of 2-methylphenylboronic acid (0.610 g) in ethanol (3 ml). The mixture was heated under reflux for 24 hours, cooled and then poured into ether (60 ml) and water (80 ml). The layers were separated and the aqueous phase extracted with a second portion of ether (60 ml). The combined organic layers were washed with water (2×50 ml), brine (50 ml) and then dried (MgSO4) and evaporated. The residue was purified by column chromatography on silica gel (50 g) eluted with ether:hexane (3:2). Combination and evaporation of suitable fractions gave the title compound as a pale brown crystalline solid, m.p. 199-202° C.

Provenance & Evidence