Methyl iodide → HCID 10537009, compound

Participants

Reaction Steps

(tert-Butoxy)-N-(6-methyl(2-pyridyl))carboxamide (20.2 g, 102 mmol) dissolved in N,N-dimethylformamide (75 ml) was slowly added to a suspension of sodium hydride (3.67 g, 153 mmol) in DMF (150 ml) at 0° C. The reaction mixture was warmed to room temperature and stirred for 1 h. Methyl iodide (9.5 ml, 153 mmol) was added dropwise at 0° C. After stirring at room temperature for 16 h, the reaction mixture was poured over ice-water and extracted with ethyl acetate. The organic layer was washed with brine, dried with sodium sulfate, filtered, and evaporated under vacuum. The crude product was chromatographed over silica gel to yield 15.3 g (66%) of (tert-Butoxy)-N-methyl-N-(6-methyl(2-pyridyl))carboxamide. NMR 1H Cl3CD δ: 7.50 (t, 1H, J=7.6 Hz), 7.37 (d, 1H, J=7.6 Hz), 6.85 (d, 1H, J=7.6 Hz), 3.38 (s, 3H), 2.48 (s, 3H), 1.50 (s, 9H).

Provenance & Evidence