Toluene → HCID 67218981, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 0.116 g of 4-(4-bromo-phenyl)-4-[5,6-difluoro-1-(2-trimethylsilanyl-ethoxymethyl)-1H-benzoimidazol-2-ylmethoxy]-piperidine-1-carboxylic acid tert-butyl ester 61 (˜0.18 mmol, 1 eq), 0.032 g of 3-cyanophenylboronic acid (0.215 mmol, 1.2 eq), and 0.040 g of Pd(PPh3)4 (0.036 mmol, 20 mol %) with 3 mL of toluene, 2 mL of ethanol and 1 mL of 2M aqueous Na2CO3 was heated at 80° C. for 20 h. The reaction was allowed to cool to room temperature, diluted with 25 mL of ethyl acetate and washed with 25 mL of saturated brine. The organic layer was dried over Na2SO4, filtered and concentrated by rotary evaporation to give the crude product which was purified by flash silica gel chromatography eluting with a gradient of 5-50% ethyl acetate in hexane to give 0.042 g of 4-(3′-cyano-biphenyl-4-yl)-4-[5,6-difluoro-1-(2-trimethylsilanyl-ethoxymethyl)-1H-benzoimidazol-2-ylmethoxy]-piperidine-1-carboxylic acid tert-butyl ester 62 as a pale foam.

Provenance & Evidence