反应 #80633

反应方程式

sodium acetate

solution

2-methyl-6-[1-[4-(methylsulfonyl)phenyl]-4-trifluoromethyl-1H-imidazol-2-yl]pyridine

hydroxylamine-O-sulfonic acid

triethylborane

→

desired product

4-[2-(6-Methylpyridin-2-yl)-4-(trifluoromethyl)-1H-imidazol-1-yl]benzenesulfonamide

溶剂

water

tetrahydrofuran

THF

反应条件

后处理

1. 1
   其他the ice bath is removed
2. 2
   workup.STIRRINGthe solution is stirred for 2 hours
3. 3
   其他is recooled to 0° C.
4. 4
   workup.STIRRINGAfter stirring for 1 hour
5. 5
   温度the reaction is heated
6. 6
   温度to reflux for 72 hours
7. 7
   workup.STIRRINGAfter stirring for 5 minutes
8. 8
   workup.STIRRINGthe mixture stirred for 24 hours
9. 9
   萃取extracted with ether
10. 10
    干燥The ethereal layer is dried over sodium sulfate
11. 11
    过滤filtered
12. 12
    浓缩concentrated
13. 13
    其他The crude solid is chromatographed on silica gel using mixtures of hexane and isopropanol

实验过程

To a clear solution of Example 34 (10 mmol) in tetrahydrofuran (60 ml) at 0° C., n-BuMgcl (2M solution in THF, 25 ml, 50 mmol) is added over 10 minutes. After stirring for an additional 20 minutes, the ice bath is removed and the solution is stirred for 2 hours. The reaction mixture is recooled to 0° C. and triethylborane (1M solution in THF, 60 ml, 60 mmol) is added. After stirring for 1 hour, the reaction is heated to reflux for 72 hours. The reaction mixture is cooled to room temperature and treated with aqueous sodium acetate (5.5 g in 22 ml water). After stirring for 5 minutes, solid hydroxylamine-O-sulfonic acid (5.5 g) is added and the mixture stirred for 24 hours. The reaction mixture is diluted with water and extracted with ether. The ethereal layer is dried over sodium sulfate, filtered and concentrated. The crude solid is chromatographed on silica gel using mixtures of hexane and isopropanol to give the desired product.

来源