Triethylamine → HCID 10282077, compound

Participants

Reaction Steps

A solution containing Intermediate 4 (500 mg, 0.97 mmol) and triethylamine (2 eq, 270 μl) in THF (10 ml) at 0° was treated dropwise with a solution of bromine (1.1 eq, 170 mg) in THF (5 ml). After 20 mins the reaction was allowed to warm to room temperature prior to dilution with EtOAc (100 ml). The crude reaction mixture was washed with saturated aqueous NaHCO3 (20 ml) and brine (20 ml), dried (MgSO4) filtered and concentrated in vacuo. The residual foam was chromatographed (SiO2; EtOAc) to give the title compound as a white powder (511 mg, 0.86 mmol, 95%). δH (CDCl3, 300K) 8.48 (2H, s), 8.05 (1H, s br), 7.52 (2H, d J 8.4 Hz), 7.04 (2H, d J 8.5 Hz), 5.81 (1H, d br, J 8.3 Hz), 4.98-4.91 (1H, m), 4.21 (2H, q, J 7.1 Hz), 3.21 (2H, d J 5.3 Hz), 1.70-1.66 (4H, m), 1.53-1.44 (4H, m), 1.28 (3H, t J 7.1 Hz), 1.20-1.16 (2H, m); m/z (ES+, 70V) 597.9 and 595.0 (MH+).

Provenance & Evidence