Sodium Carbonate → 4-Cyano-3-(2'-cyano-biphenyl-4-yl)-5-ethyl-thiophene-2-carboxylic acid ethyl ester

Participants

Reaction Conditions

Reaction Steps

Prepare a solution of 4-cyano-5-ethyl-3-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-thiophene-2-carboxylic acid ethyl ester (0.26 mmol), 2-iodobenzonitrile (41 mg, 0.18 mmol), 2M aqueous Na2CO3 (0.6 mL, 1.2 mmol) and tetrakis(triphenylphosphine)-palladium(0) (20 mg, 0.02 mmol) in 3 mL of dioxane and heat to 80° C. under nitrogen. After 3 hours cool to room temperature, dilute with 50 mL of EtOAc and wash with water (2×10 mL) and brine (1×10 mL). Dry the organics over Na2SO4, filter and evaporate. Chromatograph on silica gel (100/0 to 3/1 toluene/EtOAc) to give the title compound as a yellow foam. Yield=61 mg (91%). HPLC=80%.

Provenance & Evidence