Reaction #51670

Reaction equation

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

Solvents

N-methylpyrrolidinone

Conditions

Workup

1. 1
   workup.STIRRINGto stir
2. 2
   Otheruntil bubbling
3. 3
   workup.STIRRINGwas stirred
4. 4
   Otherto reach room temperature
5. 5
   Washthe organic layer was washed three times with brine
6. 6
   Dryingdried over magnesium sulfate
7. 7
   OtherEvaporation to dryness
8. 8
   Othergave a residue of 3.31 g which
9. 9
   Otherwas purified
10. 10
    Otherby flushing through an alumina (6% water) column
11. 11
    Washto elute the product
12. 12
    Otherafter thoroughly drying

Procedure

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.

Source