Allyltributylstannane → methyl 2-(5-allyl-3-(trifluoromethyl)-1H-pyrazol-1-yl)acetate

Participants

Reaction Conditions

Reaction Steps

Methyl 2-(5-bromo-3-(trifluoromethyl)-1H-pyrazol-1-yl)acetate (420 mg, 1.47 mmol), tri n-butyl allyltin (729 mg, 2.20 mmol) and tetrakis(triphenylphosphine)palladium(0) (50 mg, 0.043 mmol) were dissolved in DMF (10 mL). The solution was degassed with argon for 10 min and then heated at 120° C. overnight. After the solution was cooled to room temperature, the volatiles were removed under vacuum. The resulting residue was purified by silica gel chromatography (loading with toluene, eluting with dichloromethane/hexanes) to afford methyl 2-(5-allyl-3-(trifluoromethyl)-1H-pyrazol-1-yl)acetate (140 mg, 38%) as a clear oil. MS (m/z): 249.1 [M+H]+; HPLC retention time 3.51 min (2-98% acetonitrile:water with 0.05% trifluoroacetic acid).

Provenance & Evidence