1,3-Propanediol → HCID 9840796, compound

Participants

Reaction Conditions

Reaction Steps

A suspension of 6-bromo-3-[3-(pyridin-3-yl)phenyl]-3H-imidazo[4,5-b]pyridine (351 mg, 1 mmol), 3-furanboronic acid (168 mg, 1.5 mmol), tetrakis(triphenylphosphine)palladium(0) (25 mg) and 1,3-propanediol (360 μl, 5 mmol) in 1,2-dimethoxyethane (6 ml) and 2M sodium carbonate solution (3 ml) was heated at 90° C. for 16 hours. The reaction was cooled and partitioned between ethyl acetate (50 ml) and water (50 ml). The organic layer was then washed with brine, dried over anhydrous sodium sulphate, filtered and pre-adsorbed on to silica. Purification by silica gel chromatography eluting with dichloromethane/methanol/0.88 NH3 (95:4.5:0.5) furnished the title compound as a cream-coloured solid (208 mg, 62%), m.p. 191-192° C. (Found C, 73.13; H, 3.93; N, 16.01. C21H14N4O. 0.4H2O requires C, 72.99; H, 4.32; N, 16.21); δH (400 MHz, d6-DMSO) 7.17 (1H, s), 7.54-7.57 (1H, m), 7.74-7.85 (3H, m), 8.09 (1H, d, J 8), 8.22 (1H, d, J 8), 8.35 (2H, d, J 6), 8.50 (1H, s), 8.63 (1H, d, J 4), 8.80 (1H, s), 9.05 (1H, s), 9.07 (1H, s); m/z (ES+) 339 (M++H).

Provenance & Evidence