Sodium Carbonate → HCID 66697798, compound

Participants

Reaction Conditions

Reaction Steps

A solution of ethyl 1-(2-fluoropyridin-3-yl)-5-{[(trifluoromethyl)sulfonyl]oxy}-1H-pyrazole-3-carboxylate (353 mg), 4-fluorobenzenethiol (130 mg) and sodium carbonate (146 mg) in toluene (5 mL) was sufficiently deaerated. Tris(dibenzylideneacetone)dipalladium(0) (8.4 mg) and 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (11 mg) were added and the mixture was further deaerated. The mixture was stirred under an argon atmosphere at 110° C. for 3 hr, allowed to cool to room temperature, ethyl acetate was added, and the mixture was filtered through a silica gel pad. The organic layer of the filtrate was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was silica gel column chromatography (eluent:hexane-ethyl acetate=19:1→2:1) to give the title compound as a crude yellow oil (yield 203 mg).

Provenance & Evidence