Sodium Carbonate → Methyl 6-chloro-5-(2-fluoro-5-methoxyphenyl)picolinate

Participants

Reaction Conditions

Reaction Steps

Under an argon atmosphere, to a solution of methyl 5-bromo-6-chloropicolinate (12.0 g) in toluene (300 mL) was added a solution of 2-fluoro-5-methoxyphenylboronic acid (9.83 g), [1,1-bis(diphenylphosphino)ferrocene]dichloropalladium(II) dichloromethane adduct (1.00 g) and sodium carbonate (14.8 g) in water (60 mL), and the mixture was stirred at 80° C. for 2 hr. The reaction mixture was concentrated under reduced pressure and diluted with water. The reaction mixture was extracted with ethyl acetate, and the extract was washed with saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and the crude crystals were recrystallized from ethyl acetate to give the title compound (13.1 g) as pale-yellow crystals.

Provenance & Evidence