Cesium carbonate → 7-(Furan-3-yl)-3-[3-(pyridin-3-yl)phenyl]imidazo[1,2-alpha]pyridine

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Reaction Conditions

Reaction Steps

7-Chloro-3-[3-(pyridin-3-yl)phenyl]imidazo[1,2-α]pyridine (0.27 g, 0.88 mmol), 3-furanboronic acid (0.15 g, 1.33 mmol and caesium carbonate (0.58 g, 1.77 mmol) were suspended in 1,4-dioxane (5 ml) under an atmosphere of nitrogen. Tris(dibenzylideneacetone)dipalladium(0) (12 mg, 0.015 mmol) and tri-tert-butylphosphine (6.5 mg, 0.032 mmol) were then added and the mixture heated at 90° C. for 24 h. The mixture was cooled and partitioned between dichloromethane and water. The organic layer was washed with brine, dried over sodium sulphate and concentrated in vacuo to give a brown oil. Purification by flash column chromatography eluting with dichloromethane/methanol/conc. ammonia (98:2:0.2) gave the title compound (110 mg, 37%) as a pale yellow crystalline solid, m.p. 158-160° C. 1H NMR (360 MHz, CDCl3) δH 6.79 (1H, s), 6.96-7.02 (1H, m), 7.39-7.43 (1H, m), 7.52-7.56 (1H, m), 7.59-7.69 (2H, m), 7.75-7.91 (8H, m), 8.32-8.37 (1H, m), 8.63-8.68 (1H, m), 8.92 (1H, s); m/z (ES+) 338 (M++H).

Provenance & Evidence