Sodium Carbonate → 2-Bromo-6-(4-(trifluoromethyl)phenyl)pyridine

Participants

Reaction Steps

To a solution of 2,6-dibromopyridine (1.25 g, 5.28 mmol) in dimethoxyethane (100 mL) and water (50 mL), was added 4-trifluromethylphenylboronic acid (1 g, 5.27 mmol) and sodium carbonate (1.45 g, 13.7 mmol). The resulting mixture was flushed with nitrogen prior to addition of tetrakis(triphenylphosphine) palladium (0) (60 mg, 0.05 mmol). The reaction mixture was heated to reflux under nitrogen for 5 h and then allowed to attain room temperature. The solvents were removed in vacuo and the residue diluted with water (50 mL) and then extracted EtOAc (2×100 mL). The organic solution was dried (MgSO4), filtered and the solvents removed in vacuo. Purification by Biotage™ chromatography (Silica, 90 g) eluting with 4:1 cyclohexane:chloroform afforded the title compound as a white solid (0.35 g).

Provenance & Evidence