Sodium Carbonate → 5-Bromo-2-chloro-4-(2-chloro-phenyl)-pyridine

Participants

Reaction Conditions

Reaction Steps

A mixture of 10.8 g (33.9 mmol) 5-bromo-2-chloro-4-iodo-pyridine, 5.84 g (37.3 mmol) 2-chlorophenylboronic acid, 200 ml dimethoxyethane and 50 ml of a 2 M aqueous solution of sodium carbonate was deoxygenated by three freeze-thaw cycles. After addition of 381 mg (1.70 mmol) palladium(II) acetate and 917 mg (3.39 mmol) triphenylphosphine the reaction mixture was stirred at 90° C. for 4 h. Cooling to room temperature was followed by dilution with water and extraction with two portions of tert-butyl methyl ether. The combined organic extracts were washed with brine, dried with magnesium sulfate and concentrated. Column chromatography afforded 7.74 g (75%) of the title compound as a white solid.

Provenance & Evidence