反応 #51670

反応方程式

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

溶媒

N-methylpyrrolidinone

反応条件

後処理

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

実験手順

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.

出典