2,6-Dibromopyridine → 2-Bromo-6-(thiophen-3-yl)pyridine

Participants

Reaction Steps

Tetrakis(triphenylphosphine)palladium(0) (5 mol %) was added to a degassed and stirred mixture of 2,6-dibromopyridine (3.78 g, 15.6 mmol) and thiophene-3-boronic acid (2.20 g, 16.8 mmol) in tetrahydrofuran (40 ml) under an atmosphere of nitrogen then heated to reflux for 24 h. Solvent was removed in vacuo and purification by chromatography on silica gel eluting with a gradient of diethyl ether-isohexane (5-10%) gave 2-bromo-6-(thien-3-yl)pyridine (2.20 g) as a white solid: δH (400 MHz, CDCl3) 7.32-7.41 (2H, m), 7.53-7.55 (2H, m), 7.61-7.64 (1H, m), 7.94-7.96 (1H, m); m/z (ES+) 240/242 (M++H).

Provenance & Evidence