2-Bromobenzonitrile → 3'-[6-(Furan-3-yl)imidazo[4,5-b]pyridin-3-yl]biphenyl-2-carbonitrile

Participants

Reaction Conditions

Reaction Steps

A degassed mixture of crude 6-(furan-3-yl)-3-[3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)phenyl]-3H-imidazo[4,5-b]pyridine (85 mg), 2-bromobenzonitrile (54 mg, 0.3 mmol), tetrakis(triphenylphosphine)palladium(0) (10 mg) and potassium phosphate (85 mg, 0.4 mmol) in N,N-dimethylformamide (1.5 ml) was heated at 80° C. for 16 hours. The reaction was cooled to ambient temperature, diluted with dichloromethane (10 ml) and methanol (10 ml) and pre-adsorbed onto silica. Purification by silica gel chromatography eluting with dichloromethane/methanol/concentrated ammonia (96:3.5:0.5) furnished the title compound as a cream-coloured solid (31 mg). This was converted to its oxalate salt and crystallised from hot ethanol; δH (400 MHz, d6-DMSO) 7.16-7.17 (1H, m), 7.66 (1H, td, J 8 and 1), 7.70-7.72 (1H, m), 7.78-7.81 (3H, m), 7.87 (1H, td, J 8 and 1), 8.02 (1H, dd, J 8 and 1), 8.17-8.19 (1H, m), 8.25-8.26 (1H, m), 8.36 (1H, s), 8.51 (1H, d, J 2), 8.78 (1H, d, J 2), 9.02 (1H, s); m/z (ES+) 363 (M++H).

Provenance & Evidence