Methanol → 1,2-Dihydro-6-(4-fluorophenyl)-5-[4-(methylthio)phenyl]-2-oxo-pyridine-3-carbonitrile

Participants

Reaction Conditions

Reaction Steps

A solution of 26.1 g of 1-(N,N-dimethylamino)-3-(4-fluorophenyl)-2-[4-(methylthio)phenyl]prop-1-en-3-one (Step 1), 200 ml of dry DMF, 7.2 g (8.6 mMol) of the cyanoacetamide and 8 ml methanol was transferred to a dropping funnel. This solution was added dropwise to a slurry of 4.0 g of sodium hydride in 100 ml of DMF in a 3-necked round bottom flask with a magnetic stirrer and cooled with an ice bath. The temperature reached to 25° C. After complete addition of the reactants the mixture was heated to 80° C. for 4 hours, cooled and poured into one liter of 1M NaH2PO4 to give an insoluble yellow solid which was washed with water and air dried to yield 24.5 g of a yellow powder (95%).

Provenance & Evidence