Реакция #51692

Уравнение реакции

HCl

sodium hydride

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

Bromoacetonitrile

→

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

Выход 68.0%

Растворители

water

dimethylformamide

Условия реакции

Обработка

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

Методика

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.

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