Hydrochloric Acid → 6-Bromo-1-cyanomethyl-1H-indole-3-carboxylic Acid

HRID 23414Notes

Reaction equation

[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([C:11]([OH:13])=[O:12])=[CH:7][NH:8]2)=[CH:4][CH:3]=1.[H-].[Na+].Br[CH2:17][C:18]#[N:19].Cl>CN(C)C=O.O>[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([C:11]([OH:13])=[O:12])=[CH:7][N:8]2[CH2:17][C:18]#[N:19])=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 0 °C

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.

Workup

stirringwas stirred at this temperature until no more bubbles
custom(ca. 20-30 minutes)
temperatureto warm to room temperature over the next hour
customa precipitate formed
customWhen dried the product
customto be used directly in the next step without further purification

Sources & evidence

ORD record: ord-e4124114688942ac9062624f8cc731ac
Source dataset: uspto-grants-2005_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06852726B2

Reaction notes

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