Reacción #51670

Ecuación de reacción

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

Disolventes

N-methylpyrrolidinone

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.STIRRINGto stir
2. 2
   Otrountil bubbling
3. 3
   workup.STIRRINGwas stirred
4. 4
   Otroto reach room temperature
5. 5
   Lavadothe organic layer was washed three times with brine
6. 6
   Secadodried over magnesium sulfate
7. 7
   OtroEvaporation to dryness
8. 8
   Otrogave a residue of 3.31 g which
9. 9
   Otrowas purified
10. 10
    Otroby flushing through an alumina (6% water) column
11. 11
    Lavadoto elute the product
12. 12
    Otroafter thoroughly drying

Procedimiento

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.

Fuente