反应详情

温度

0 °C

To a solution of 3-methyl-5-(1-[4-(methylsulfonyl)phenyl]-4-(trifluoromethyl)-1H-imidazol-2-yl]pyridine (Example 39) (1.9 mmol) in 25 mL of dry THF was added n-BuMgCl (3.8 mL of 2.0 M THF solution, 7.5 mmol) slowly at 0° C. After stirring for additional 15 minutes, the solution was stirred at room temperature for 2 hours. The reaction mixture was re-cooled to 0° C. and triethylborane (9.5 mL of 1.0 M THF solution, 9.5 mmol) was added. After stirring at for 2 hours, the mixture was heated to reflux for 72 hours. The reaction mixture was cooled to room temperature and treated with a solution of sodium acetate (2.3 g) in 10 mL of water. After stirring for 5 minutes, hydroxylamine-O-sulfonic acid (2.3 g) was added and the mixture was stirred for 20 hours. The reaction mixture was extracted with ether (2×100 mL). The ethereal layer was dried over MgSO4, filtered and concentrated in vacuo. The crude product was purified by chromatography on silica gel (isopropanol/toluene, 5:95) to give 0.07 g of 4-[2-(5-methylpyridin-3-yl)-4-(trifluoromethyl)-1H-imidazol-1-yl]benzenesulfonamide as a colorless solid (8%): mp 242–243° C. Anal. Calc'd. For C16H13F3N4O2S: C, 50.26, H, 3.43, N, 14.65, S, 8.39. Found: C, 50.02, H, 3.63, N, 14.26, S, 8.41.

1. stirringthe solution was stirred at room temperature for 2 hours
2. stirringAfter stirring at for 2 hours
3. temperaturethe mixture was heated
4. temperatureto reflux for 72 hours
5. temperatureThe reaction mixture was cooled to room temperature
6. stirringAfter stirring for 5 minutes
7. stirringthe mixture was stirred for 20 hours
8. extractionThe reaction mixture was extracted with ether (2×100 mL)
9. dry with materialThe ethereal layer was dried over MgSO4
10. filtrationfiltered
11. concentrationconcentrated in vacuo
12. customThe crude product was purified by chromatography on silica gel (isopropanol/toluene, 5:95)