Sodium Carbonate → 3-(4-((Tert-butyl(dimethyl)silyl)oxy)-2'-fluoro-5'-methoxybiphenyl-2-yl)-2,2-dimethylpropanenitrile

Participants

Reaction Conditions

Reaction Steps

Under a nitrogen atmosphere, to a solution of 3-(2-bromo-5-((tert-butyl(dimethyl)silyl)oxy)phenyl)-2,2-dimethylpropanenitrile (903 mg), 2-fluoro-5-methoxyphenylboronic acid (621 mg), tris(dibenzylideneacetone)dipalladium(0) (45 mg) and 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl (79 mg) in toluene (10 mL) was added 2.0 M aqueous sodium carbonate solution (3.7 mL), and the mixture was stirred at 90° C. for 3 hr. The reaction mixture was filtered through celite, water was added to the filtrate, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure and the residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound as a crude product. This compound was used for the next step without further purification.

Provenance & Evidence