Triethylamine → 3-(2'-Cyanobiphenyl-3-yl)imidazo[1,2-alpha]pyridine-7-carbonitrile

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Reaction Steps

3′-(7-Hydroxyiminomethylimidazo[1,2-α]pyridin-3-yl)biphenyl-2-carbonitrile (105 mg, 0.31 mmol), triethylamine (157 mg, 1.55 mmol) and 1,1′-carbonyldiimidazole (252 mg, 1.55 mmol) were dissolved in dichloromethane (5 ml) and stirred at room temperature for 15 min then heated under reflux for 2.5 h. The mixture was cooled to ambient temperature, diluted with dichloromethane (40 ml) and washed with water (40 ml) and brine (40 ml). The organics were dried over anhydrous sodium sulfate and evaporated to dryness. Purification of this material by preparative thin-layer chromatography eluting with dichloromethane/methanol/conc. ammonia (98:2:0.2) gave the title compound (85 mg, 86%) as a white solid. 1H NMR (400 MHz, CDCl3) δH 7.03 (1H, dd, J 1 and 7), 7.52 (1H, dt, J 8 and 1), 7.58 (1H, d, J 7), 7.62-7.66 (2H, m), 7.69-7.74 (2H, m), 7.79-7.84 (2H, m), 7.97 (1H, s), 8.12 (1H, s), 8.69 (1H, d, J 7); m/z (ES+) 321 (M++H).

Provenance & Evidence