Pyridine → HCID 57767014, compound

Participants

Reaction Steps

Sodium hydride (2.5 equiv., 0.950 mmol, 0.038 g (60%)) was added to a solution of malonitrile (1.2 equiv., 0.456 mmol, 0.030 g) in dry pyridine (1 ml) under Ar atmosphere. The catalyst—prepared as described above—was injected, and the mixture was stirred at room temperature for 5 min. 6-(6-Bromo-pyridin-3-yl)-9-methoxypyrido[2′,1′:2,3]imidazo[4,5-c]isoquinolin-5(6H)-one (39) (1.0 equiv., 0.380 mmol, 0.160 g) was then added and the reaction mixture was heated at 85° C. for 2 h. After destruction of the excess of sodium hydride with methanol, the solvent was concentrated under vacuum. The residue was purified by column chromatography (gradient elution: dichloromethane/methanol (7M NH3) 9:1→8:2) to give α-cyano-5-[5,6-dihydro-9-methoxy-5-oxo-pyrido[2′,1′:2,3]imidazo[4,5-c]isoquinolin-6-yl]-2-pyridineacetonitrile (52) (0.030 g, yield=19%, purity (LC)=99%).

Provenance & Evidence