反应 #51670

反应方程式

water ethyl acetate

Sodium hydride

7-chloro-3-methanesulfonyl-1H-indole

7-Chloro-3-methanesulfonyl-1H-indole

Bromoacetonitrile

→

(7-Chloro-3-methanesulfonyl-indol-1-yl)-acetonitrile

溶剂

N-methylpyrrolidinone

反应条件

后处理

1. 1
   workup.STIRRINGto stir
2. 2
   其他until bubbling
3. 3
   workup.STIRRINGwas stirred
4. 4
   其他to reach room temperature
5. 5
   洗涤the organic layer was washed three times with brine
6. 6
   干燥dried over magnesium sulfate
7. 7
   其他Evaporation to dryness
8. 8
   其他gave a residue of 3.31 g which
9. 9
   其他was purified
10. 10
    其他by flushing through an alumina (6% water) column
11. 11
    洗涤to elute the product
12. 12
    其他after thoroughly drying

实验过程

The 7-chloro-3-methanesulfonyl-1H-indole (2.21 g, 0.00962 mole) of Step 6 was dissolved in 20 ml dry N-methylpyrrolidinone and cooled to 0° C. under a nitrogen atmosphere. Sodium hydride (60% in oil, 0.46 g, 0.0115 mole) was added in portions with stirring and the reaction mixture was allowed to stir until bubbling ceased. Bromoacetonitrile (1.27 g, 0.0106 mole) was added all at once and the resulting solution was stirred and allowed to reach room temperature. After 1 h, the reaction mixture was poured into water-ethyl acetate and the organic layer was washed three times with brine and dried over magnesium sulfate. Evaporation to dryness gave a residue of 3.31 g which was purified by flushing through an alumina (6% water) column using 3:7 and 1:1 ethyl acetate-hexane to elute the product. The purified (7-chloro-3-methanesulfonyl-indol-1-yl)-acetonitrile was crystalline and weighed 2.111 g after thoroughly drying.

来源