Potassium Carbonate → (S)-tert-Butyl 1-cyano-2-(4'-cyano-3'-fluorobiphenyl-4-yl)ethylcarbamate

Participants

Reaction Steps

A solution of 4-cyano-3-fluorophenylboronic acid (0.736 g) dissolved in dioxane (10 mL) was added to a stirred solution of (S)-tert-butyl 1-cyano-2-(4-iodophenyl)ethylcarbamate (1.51 g) and bis[bis(1,2-diphenylphosphino)ethane]palladium (0) (0.037 g) in dioxane (20 mL) under nitrogen. The resulting mixture was stirred for 10 min. A solution of potassium carbonate (1.121 g) in water (5 mL) was added and the resulting solution was stirred at 75° C. for 3 h. The cooled mixture was evaporated to dryness. The residue was taken up in ethyl acetate (150 mL) and washed with saturated brine (3×50 mL), dried over sodium sulfate and adsorbed onto silica. The crude product was purified by flash silica chromatography, eluting with 20% ethyl acetate in isohexane. Pure fractions were evaporated to dryness to afford the subtitle compound as a colourless solid (0.568 g).

Provenance & Evidence