Reaction #51692

Reaction equation

HCl

sodium hydride

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

Bromoacetonitrile

→

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

Yield 68.0%

Solvents

water

dimethylformamide

Conditions

Workup

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

Procedure

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.

Source