2,6-Dibromopyridine → 6-Bromo-2,4'-bipyridine

Participants

Reaction Steps

4-Tri-n-butylstannylpyridine (3.30 g, 8.9 mmol) was added to a degassed and stirred solution of 2,6-dibromopyridine (2.00 g, 8.3 mmol) and tetrakis(triphenylphosphine)palladium(0) (5 mol %) in tetrahydrofuran (30 ml) under an atmosphere of nitrogen then heated to reflux for 48 h. Solvent was removed in vacuo and purification by chromatography on silica gel eluting with dichloromethane followed by trituration with isohexane gave 6-bromo-2,4′-bipyridinyl (1.05 g) as a white solid: δH (400 MHz, CDCl3) 7.52-7.57 (1H, m), 7.66-7.70 (1H, m), 7.86 (2H, m), 8.10-8.50 (1H, m), 8.72-8.76 (1H, m), 8.77-8.81 (1H, m); m/z (ES+) 234/236 (M++H).

Provenance & Evidence