反应 #80648

反应方程式

3-[1-[4-[[2-(trimethylsilyl)ethyl]sulfonyl]phenyl]-4-(trifluoromethyl)-1H-imidazol-2-yl]pyridine

n-Bu4NF

sodium acetate

hydroxylamine-O-sulfonic acid

→

3-[1-[4-[[2(Trimethylsilyl)ethyl]sulfonyl]phenyl]-4-(trifluoromethyl)-1H-imidazol -2-yl]pyridine

4-[2-(pyridin-3-yl)-4-(trifluoromethyl)-1H-imidazol-1-yl]benzenesulfonamide

收率 173.5%

溶剂

THF

Water

ethyl acetate

water

反应条件

后处理

1. 1
   温度The mixture was heated
2. 2
   温度to reflux for 1 hour
3. 3
   其他The organic phase was separated
4. 4
   洗涤washed with saturated NaHCO3 solution, water, brine
5. 5
   干燥dried over HgSO4
6. 6
   过滤filtered
7. 7
   浓缩The filtrate was concentrated
8. 8
   其他the residue was purified by chromatography on silica gel (ethyl acetate/acetone, 95:5)

实验过程

3-[1-[4-[[2(Trimethylsilyl)ethyl]sulfonyl]phenyl]-4-(trifluoromethyl)-1H-imidazol -2-yl]pyridine was prepared from Example 30 with a method similar to that described in Example 48, Step 1. To a solution of 3-[1-[4-[[2-(trimethylsilyl)ethyl]sulfonyl]phenyl]-4-(trifluoromethyl)-1H-imidazol-2-yl]pyridine (0.200 g, 0.46 mmol) in 1.0 mL of dry THF was added n-Bu4NF (1.38 mL of 1.0H THF solution, 1.38 mmol). The mixture was heated to reflux for 1 hour and cooled to room temperature. A solution of sodium acetate (0.17 g, 2.1 mmol) in 3 mL of water and hydroxylamine-O-sulfonic acid (0.26 g, 2.3 mmol) were added sequentially and the mixture was stirred for 1 hour. Water (7 mL) and ethyl acetate (7 mL) were added. The organic phase was separated and washed with saturated NaHCO3 solution, water, brine, dried over HgSO4 and filtered. The filtrate was concentrated and the residue was purified by chromatography on silica gel (ethyl acetate/acetone, 95:5) to give 0.147 g of 4-[2-(pyridin-3-yl)-4-(trifluoromethyl)-1H-imidazol-1-yl]benzenesulfonamide as a colorless solid (87%): mp(DSC) 213°-215 ° C. Anal. Calc'd. for C15H11F3N4O2S: C, 48.91; H, 3.01; N, 15.21; S, 8.71. Found: C, 48.58; H, 2.99; N, 14.87; S, 8.85.

来源