Benzyl Bromide → HCID 86665675, compound

Participants

Reaction Steps

Cesium carbonate (39.3 mg, 0.120 mmol) was added to a solution of 2-chloro-6-cyclopentyl-4-(4-hydroxyphenyl)nicotinonitrile (18 mg, 0.060 mmol) and benzyl bromide (0.014 mL, 0.120 mmol) in DMSO (1 mL). After 16 h at room temperature, the mixture was diluted with ethyl acetate (80 mL), washed with saturated sodium bicarbonate (5 mL), brine (5 mL), dried (MgSO4) and concentrated. Silica gel chromatography, eluting with 0-15% ethyl acetate in hexanes, gave 4-(4-(benzyloxy)phenyl)-2-chloro-6-cyclopentylnicotinonitrile as a white solid (20 mg, 85% yield). 1H NMR (400 MHz, CDCl3) δ ppm 7.50-7.74 (2H, m), 7.30-7.48 (5H, m), 7.19 (1H, s), 7.00-7.15 (2H, m), 5.13 (2H, s), 3.10-3.34 (1H, m), 2.00-2.32 (2H, m), 1.64-1.95 (6H, m), MS (ES+) m/z: 389 (M+H); LC retention time: 4.431 min (analytical HPLC Method A).

Provenance & Evidence