Water → HCID 9907479, compound

Participants

Reaction Conditions

Reaction Steps

Methyltriphenylphosphonium bromide (304 mg, 0.85 mmol) was suspended in dry diethyl ether (5 ml) in a nitrogen-flushed flask and cooled to -5° C. n-Butyl lithium (0.34 ml, 2.5M in hexanes) was added dropwise producing a yellow colour. The mixture was warmed to room temperature before heating to reflux for 1 hr. The amber homogeneous solution thus obtained was cooled to -78° C. and 3-cyano-4-(3-oxocyclobutyl)-1-(2,6-dichloro-4-trifluoromethylphenyl)pyrazole (300 mg, 0.80 mmol, Example 3), dissolved in dry diethyl ether (5 ml), added dropwise keeping the internal temperature at ca. -70° C. The mixture was allowed to slowly warm to room temperature before refluxing for 1 hr. The mixture was then cooled, poured into water (20 ml) and extracted with diethyl ether (3×10 ml). The combined organics were washed with brine, dried (MgSO4), filtered and ether solvent evaporated in vacuo. The residue was purified by silica chromatography (eluting with 20% DCM/hexane) yielding 40 mg of a white solid. This was further purified by hplc (Microsorb™C18, eluting with acetonitrile/methanol/water 6:1:3 v/v) to give 18 mg of the title compound.

Provenance & Evidence