Methyl cyanoacetate → HCID 67288378, compound

Participants

Reaction Conditions

Reaction Steps

NMP (7 mL) was added to a round bottom, placed under nitrogen and cooled to 0° C. NaH (1.16 g, 29.1 mmol) was added portionwise followed by the addition of methyl cyanoacetate (1.31 ml, 14.5 mmol) (in 3 mL of NMP) dropwise. After stirring for 30 minutes at 0° C., 2-bromo-3,5-dichloropyridine (3.0 g, 13.2 mmol) was added and the reaction was heated to 130° C. for 5 hours. The reaction was allowed to cool, poured into ice and extracted twice with ethyl acetate. The ethyl acetate was combined, dried over MgSO4, filtered and concentrated. The amorphous material was crystallized from methanol to afford the desired compound (700 mg, 2.86 mmol, 21.6% yield) as light brown needles.

Provenance & Evidence