Sodium sulfate decahydrate → 3-[3-(Pyridin-3-yl)phenyl]imidazo[1,2-alpha]pyridin-7-ylmethanol

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Reaction Conditions

Reaction Steps

3-[3-(Pyridin-3-yl)phenyl]imidazo[1,2-α]pyridine-7-carboxylic acid methyl ester (2.0 g, 6.1 mmol) was suspended in tetrahydrofuran (75 ml) and cooled to 0° C. before adding lithium aluminium hydride (9.1 ml of 1.0M solution in tetrahydrofuran) dropwise over 5 minutes. The mixture was allowed to warm to ambient temperature and stirring continued for 2 h. Sodium sulphate decahydrate (10 g) was then added portionwise and the resulting suspension stirred for a further 1 h. The mixture was diluted with methanol and pre-adsorbed on to silica. Purification by flash column chromatography on silica eluting with dichloromethane/methanol/conc. ammonia (gradient 99:1:0.1 through to 95:5:0.3) gave the title compound (1.25 g, 68%) as a white solid. 1H NMR (360 MHz, CDCl3) δH 4.78 (2H, s), 6.87 (1H, dd, J 7 and 1), 7.37-7.43 (1H, m), 7.56-7.75 (6H, m), 7.89-7.95 (1H, m), 8.33 (1H, d, J 7), 8.63 (1H, dd, J 1 and 7), 8.89 (1H, s); m/z (ES+) 302 (M++H).

Provenance & Evidence