Ethyl 3-bromoindole-7-carboxylate → 3-Cyano-1H-indole-7-carboxylic acid

HRID 971074Notes

Reaction equation

HRID 971074 reaction equation
Br[C:2]1[C:10]2[C:5](=[C:6]([C:11]([O:13]CC)=[O:12])[CH:7]=[CH:8][CH:9]=2)[NH:4][CH:3]=1.[C:16]([Cu])#[N:17]>CN1C(=O)CCC1>[C:16]([C:2]1[C:10]2[C:5](=[C:6]([C:11]([OH:13])=[O:12])[CH:7]=[CH:8][CH:9]=2)[NH:4][CH:3]=1)#[N:17]

Participants

4

Reactant 2

HCID 17933196Ethyl 3-bromoindole-7-carboxylateHCID 178418546HCID 178418546, compound

Product 1

HCID 113674313-Cyano-1H-indole-7-carboxylic acid

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
120 °C

Procedure

7 g of ethyl 3-bromoindole-7-carboxylate are dissolved in 70 g of NMP, and 4 g of CuCN are added. The mixture is heated to 100-140° C. with stirring. After 3 hours, the mixture is subjected to conventional work-up, giving 3-cyanoindole-7-carboxylic acid.

Sources & evidence

ORD record
ord-e3bf35874ded474188a9606433d30327
Source dataset
uspto-grants-2007_12
Patent number
US07312342B2

Reaction notes

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