Triphenylphosphine → 1-(4-Bromopyridin-2-yl)ethanamine

Participants

Reaction Steps

To a solution of 2-(1-azidoethyl)-4-bromopyridine (4.08 g, 16.54 mmol) in THF (100 mL) and water (10 mL) was added polymer-bound triphenylphosphine (200-400 mesh, -3 mmol/g loading; 10.97 g, 32.94 mmol). The suspension was then stirred at room temperature for 7 hours. The reaction was filtered over a coarse frit twice, then concentrated to afford the crude product which was used without further purification. 1H NMR (400 MHz, CDCl3) δ 8.35 (d, J=5.2 Hz, 1H), 7.52 (s, 1H), 7.32 (dd, J=5.2, 1.6 Hz, 1H), 4.13 (q, J=6.7 Hz, 1H), 1.83 (br s, 2H), 1.41 (d, J=6.7 Hz, 3H).

Provenance & Evidence