Sodium Carbonate → 1-((4-((Tert-butyl(dimethyl)silyl)oxy)-2'-fluoro-5'-methoxybiphenyl-2-yl)methyl)cyclopentanecarbonitrile

Participants

Reaction Conditions

Reaction Steps

Under a nitrogen atmosphere, to a solution of 1-(2-bromo-5-((tert-butyl(dimethyl)silyl)oxy)benzyl)cyclopentanecarbonitrile (471 mg), 2-fluoro-5-methoxyphenylboronic acid (361 mg), tris(dibenzylideneacetone)dipalladium(0) (23 mg) and 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl (39 mg) in toluene (5.0 mL) was added 2.0M aqueous sodium carbonate solution (1.8 mL), and the mixture was stirred at 90° C. for 1 hr. Water was added to the reaction mixture, 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 a crude product of the title compound. The obtained crude product was directly used for the next step.

Provenance & Evidence