反应详情

A stirred, cooled (ice bath) solution of 3-bromo-N-cyclopropyl-4-methyl-benzamide (Intermediate 95, 6 g, 23.25 mmol) in anhydrous tetrahydrofuran (100 mL) under argon was treated with small portions of sodium hydride (1.6 g, 40 mmol, 60% dispersion in mineral oil). The reaction mixture was allowed to warm to ambient temperature and after 1 h, methyl iodide (3.11 mL, 50 mmol) was added and the reaction mixture was refluxed for 5 h. It was cooled to ambient temperature, poured into cold water and extracted with diethyl ether (×2). The combined organic phase was dried over anhydrous magnesium sulfate, filtered and evaporated in vacuo to afford the title product as a dirty brown solid that was used as such for the next step (6.3 g, ˜100%).

1. temperaturethe reaction mixture was refluxed for 5 h
2. temperatureIt was cooled to ambient temperature
3. extractionextracted with diethyl ether (×2)
4. dry with materialThe combined organic phase was dried over anhydrous magnesium sulfate
5. filtrationfiltered
6. customevaporated in vacuo