Potassium Phosphate, Tribasic → tert-Butyl 4-(1-(2-(pyrrolidin-1-yl)ethyl)-4-vinyl-1H-imidazol-2-yl)piperidine-1-carboxylate

Participants

Reaction Steps

Add tert-butyl 4-(4-bromo-1-(2-(pyrrolidin-1-yl)ethyl)-1H-imidazol-2-yl)piperidine-1-carboxylate (0.26 g, 0.60 mmol) in 1,4-dioxane (4 mL) and water (1 mL). Add potassium phosphate, tribasic, N-hydrate (0.26 g, 2.0 eq) and dicyclohexyl-[2-(2,6-dimethoxyphenyl)phenyl]phosphane (0.036 g, 0.15 eq). Add 4,4,5,5-tetramethyl-2-vinyl-1,3,2-dioxaborolane (0.22 mL, 2.05 eq) and degas for 10 minutes. Add bis(dibenzylideneacetone)palladium(0) (0.03 g, 0.06 eq) and reflux at 150° C. for 1 hour. Filter through Celite®. Wash with dichloromethane. Concentrate the filtrate to dryness in vacuo. Purify by silica gel chromatography, eluting with 25% methanol/ethyl acetate, to give the title compound as a yellow foam (0.14 g, 38%). MS (ES) m/z=375 [M]+.

Provenance & Evidence