Potassium Phosphate, Tribasic → [1,1'-Biphenyl]-2-carbonitrile, 3'-imidazo[1,2-a]pyrazin-3-yl-

Participants

Reaction Conditions

Reaction Steps

A mixture of 3-bromoimidazo[1,2-α]pyrazine (150 mg, 0.76 mmol), potassium phosphate (321 mg, 1.51 mmol) and 3′-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)biphenyl-2-carbonitrile (3 ml of a 0.5M solution in N,N-dimethylacetamide) were degassed with N2 for 15 min. Tetrakis(triphenylphosphine)palladium(0) (44 mg, 0.04 mmol) was added and the mixture heated at 80° C. for 18 h. The reaction was allowed to cool to room temperature, diluted with water (20 ml) and saturated sodium hydrogencarbonate solution (20 ml) then extracted with ethyl acetate (2×75 ml). The combined organic fractions were washed with brine (40 ml), dried over anhydrous sodium sulfate and evaporated to give a black oil. The oil was purified by silica gel chromatography eluting with dichloromethane and 1% 0.88 ammonia on a gradient of methanol (1-2%). The solid obtained was triturated with diethyl ether which gave 3′-(imidazo[1,2-α]pyrazin-3-yl)biphenyl-2-carbonitrile (83 mg, 37%) as a white powder: δH (400 MHz, CDCl3) 7.52 (1H, td, J 8 and 1), 7.58 (1H, dd, J 8 and 1), 7.61-7.74 (4H, m), 7.80-7.85 (2H, m), 7.94-7.97 (2H, m), 8.55 (1H, d), 9.18 (1H, s).

Provenance & Evidence