Potassium Phosphate, Tribasic → HCID 22727960, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 3-(6-bromoimidazo[4,5-b]pyridin-3-yl)phenol (2.32 g, 8 mmol), 3-furanboronic acid (1.43 g, 12.8 mmol), potassium phosphate (3.4 g, 16 mmol) and tetrakis(triphenylphosphine)palladium(0) (370 mg) in degassed N,N-dimethylformamide (12 ml) was heated at 80° C. for 20 hours. After cooling to ambient temperature the mixture was dissolved in 3N sodium hydroxide and extracted with dichloromethane, then with ether. The aqueous phase was adjusted to pH 7 with concentrated hydrochloric acid and the resulting solid collected by filtration, washed with water and dried under high vacuum to afford 3-[6-(furan-3-yl)imidazo[4,5-b]pyridin-3-yl]phenol as a cream-coloured solid (2.2 g, 99%); δH (400 MHz, d6-DMSO) 6.86 (1H, ddd, J 8, 2 and 1), 7.15 (1H, s), 7.33-7.45 (3H, m), 7.81 (1H, s), 8.35 (1H, s), 8.46 (1H, d, J 2), 8.54 (1H, d, J 2), 8.91 (1H, s), 9.94 (1H, br s); m/z (ES+) 278 (M++H).

Provenance & Evidence