Dimethylformamide → HCID 178461223, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 6-chloro-4-(cyclobutylmethoxy)-3-[(trans-4-methylcyclohexyl)methyl]-2-[(3R)-3-phenylmorpholin-4-yl]-3H-imidazo[4,5-c]pyridine (120 mg, 0.23 mmol) in DMF (1.5 mL) was added Zn(CN)2 (83 mg, 0.70 mmol), and the mixture was deoxygenated by purging with nitrogen for 10 minutes. Pd(dppf)Cl2 dichloromethane adduct (57.7 mg, 0.07 mmol) was added and the reaction was again deoxygenated for 5 minutes. The reaction flask was sealed and the mixture was heated at 140° C. for 16 h. The reaction mixture was then cooled to room temperature, diluted with EtOAc (50 mL), and the organic layer was separated. The organic layer was washed with water (2×50 mL) followed by saturated brine solution (2×30 mL), dried over anhydrous Na2SO4, filtered, and concentrated. The residue was purified by silica gel chromatography (40% EtOAc/petroleum ether) to yield 4-(cyclobutylmethoxy)-3-[(trans-4-methylcyclohexyl)methyl]-2-[(3R)-3-phenylmorpholin-4-yl]-3H-imidazo[4,5-c]pyridine-6-carbonitrile. MS ES/APCI calc'd. for C30H37N5O2 [M+H]+ 500. found 500.

Provenance & Evidence