Methyl iodide → HCID 68705964, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of pyridine-2,5-diol (1.0 g, 9.0 mmol) in dimethylformamide (150 mL) at 0° C. was added sodium hydride (60% dispersion in mineral oil, 0.30 g, 9.0 mmol) in portions, and the reaction stirred at 0° C. for 1 hour. To this reaction was added 5-bromo-3-nitropicolinonitrile (2.05 g, 9.00 mmol) and the reaction stirred overnight at ambient temperature. Sodium hydride (60% dispersion in mineral oil, 0.30 g, 9.0 mmol) was added to the reaction mixture in portions, followed by methyl iodide (2.56 g, 18.00 mmol), and the reaction was stirred at ambient temperature for 3 hours. The reaction was poured into water and the aqueous layer extracted with ethyl acetate. The organics were washed with 1N HCl, 1M NaOH, water, brine, dried over magnesium sulfate and concentrated in vacuo. The material purified over silica gel (2% ethyl acetate/dichloromethane) to afford 5-bromo-3-(1-methyl-6-oxo-1,6-dihydropyridin-3-yloxy)picolinonitrile (1.5 g, 54%).

Provenance & Evidence