Diethyl Ether → HCID 22120921, compound

Participants

Reaction Steps

To a rapidly stirred solution of 5-amino-3-cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)-4-iodopyrazole (0.335 g) in toluene (2 ml) containing tetrakis(triphenylphosphine)palladium(0) (0.03 g) was added saturated aqueous sodium hydrogen carbonate solution (1 ml) and a solution of 3,4-dimethoxyphenylboronic acid (0.273 g) in ethanol (1 ml). The mixture was heated under reflux for 5 hours, cooled and then poured into ether (25 ml) and water (25 ml). The organic layer was separated, washed with water (2×25 ml), brine (25 ml) and then dried (MgSO4) and evaporated. The residue was purified by column chromatography on silica gel (30 g) eluted with dichloromethane: ethanol (99:1). Combination and evaporation of suitable fractions gave the title compound as a pale pink crystalline solid, m.p. 250° C.

Provenance & Evidence