Sodium Carbonate → 3-(Benzyloxy)-5-(((tert-butyldimethylsilyl)oxy)methyl)-2-(2-fluoro-5-methoxyphenyl)pyridine

Participants

Reaction Conditions

Reaction Steps

Under an argon atmosphere, to a solution of 3-(benzyloxy)-5-(((tert-butyldimethylsilyl)oxy)methyl)-2-chloropyridine (2.53 g) in toluene (20 mL) were added 2-fluoro-5-methoxyphenylboronic acid (1.77 g), tris(dibenzylideneacetone)dipalladium(0) (255 mg), 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl (457 mg) and 2.0 M aqueous sodium carbonate solution (10.4 ml), and the mixture was stirred at 90° C. for 3 hr. The reaction mixture was filtered through celite, and water was added at room temperature. The reaction mixture was extracted with ethyl acetate, and the extract was washed with water and saturated brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (2.81 g) as a pale-yellow oil.

Provenance & Evidence