Water → HCID 9857533, compound

Participants

Reaction Steps

3-(7-Methylimidazo[1,2-α]pyridin-3-yl)phenol (310 mg, 1.4 mmol) in anhydrous N,N-dimethylformamide (5 ml) was treated with sodium hydride (60% dispersion in mineral oil, 70 mg, 1.75 mmol) and then stirred at ambient temperature for 30 minutes. 2-Bromopyridine (0.16 ml, 1.67 mmol) was added and the reaction mixture heated at 120° C. for 4 days, poured into water (25 ml) and extracted with ethyl acetate (2×30 ml). The combined organic phases were washed with water (3×20 ml), dried over anhydrous magnesium sulphate and concentrated in vacuo. Purification by preparative TLC gave the title compound as a colourless oil (100 mg, 24%). 1H NMR (400 MHz, CDCl3) δH 2.64 (3H, s), 7.08-7.10 (1H, m), 7.14-7.17 (1H, m), 7.33-7.37 (2H, m), 7.50-7.55 (2H, m), 7.66-7.70 (1H, m), 7.78 (1H, s), 7.85-7.90 (1H, m), 8.07 (1H, s), 8.15-8.16 (1H, m), 8.65 (1H, d, J 7); m/z (ES+) 302 (M++H).

Provenance & Evidence