Potassium Phosphate, Tribasic → HCID 178518664, compound

Participants

Reaction Conditions

Reaction Steps

4-(2-Oxo-3-(2-(piperidin-1-yl)ethyl)-2,3-dihydro-1H-imidazo[4,5-b]pyrazin-5-yl)benzonitrile. 6-Bromo-1-(2-(piperidin-1-yl)ethyl)-1H-imidazo[4,5-b]pyrazin-2(3H)-one (1.2 g., 3.68 mmol), 4-cyanophenylboronic acid (0.595 g., 4.05 mmol), dichloro[1,1′-bis(diphenylphosphino)ferrocene]palladium(II) dichloromethane adduct (0.3 g., 0.368 mmol) and potassium phosphate (3.12 g., 14.7 mmol) were combined in DMF (9 mL) and heated in a sealed tube to 100° C. overnight. The flask was cooled to rt and the reaction mixture was filtered through celite, washed with methanol and ethyl acetate. The filtrate and washes were combined, concentrated and treated with water. The product was extracted into ethyl acetate, the organic layer was concentrated and the resulting material was subjected to silica gel chromatography (60-100% ethyl acetate in hexanes) to yield the title compound (0.5 g., 39% yield). MS (ESI) m/z 349.3[M+1]+.

Provenance & Evidence