Reacción #51692

Ecuación de reacción

HCl

sodium hydride

6-Bromo-1H-indole-3-carboxylic acid

Bromoacetonitrile

→

6-Bromo-1-cyanomethyl-1H-indole-3-carboxylic acid

Rendimiento 68.0%

Disolventes

water

dimethylformamide

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.STIRRINGwas stirred at this temperature until no more bubbles
2. 2
   Otro(ca. 20-30 minutes)
3. 3
   Temperaturato warm to room temperature over the next hour
4. 4
   Otroa precipitate formed
5. 5
   OtroWhen dried the product
6. 6
   Otroto be used directly in the next step without further purification

Procedimiento

6-Bromo-1H-indole-3-carboxylic acid (0.24 g, 1 mmole) was dissolved in anhydrous dimethylformamide (2 ml) and cooled to 0° C. in a nitrogen atmosphere. With stirring, sodium hydride (60% in oil, 0.088 g, 2.2 mmole) was added all at once and the mixture was stirred at this temperature until no more bubbles evolved (ca. 20-30 minutes). Bromoacetonitrile (0.132 g, 1.1 mmole) was added to the reaction mixture which was then allowed to warm to room temperature over the next hour. The reaction mixture was poured into water, acidified with HCl and a precipitate formed. When dried the product weighed 0.190 g (68% yield) and was sufficiently pure to be used directly in the next step without further purification.

Fuente