Trimethylsilylacetylene → HCID 21188087, compound

Participants

Reaction Steps

To a stirred solution of 5-amino-1-(2,6-dichloro-4-trifluoromethylphenyl)-4-iodo-3-trifluoromethylpyrazole (28 g) in triethylamine (120 ml) and dimethylformamide (24 ml) at room temperature was added trimethylsilylacetylene (12 ml), cuprous iodide (0.6 g) and bis(triphenylphosphine)palladium(II) chloride (1.2 g). The mixture was heated under reflux for 4 hours and then left at room temperature overnight. The reaction mixture was diluted with water (500 ml) and ether (500 ml) and filtered. The filtrate's organic layer was separated, dried (MgSO4) and evaporated to give the crude product as an oil which was purified by column chromatography on silica gel eluted with dichloromethane:hexane (1:1). Combination and evaporation of appropriate fractions, followed by recrystallisation from hexane, provided the title compound as a buff solid, m.p. 120-123° C.

Provenance & Evidence