Benzonitrile, 3-(bromomethyl)- → 4-methyl-1H-indole-2-carboxylic acid 3-cyano-benzyl ester

HRID 1250396Notes

Reaction equation

HRID 1250396 reaction equation
[CH3:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[C:5]([C:11]([OH:13])=[O:12])[NH:6]2.[C:14]([C:16]1[CH:17]=[C:18]([CH:21]=[CH:22][CH:23]=1)[CH2:19]Br)#[N:15]>CN(C)C=O>[C:14]([C:16]1[CH:17]=[C:18]([CH:21]=[CH:22][CH:23]=1)[CH2:19][O:12][C:11]([C:5]1[NH:6][C:7]2[C:3]([CH:4]=1)=[C:2]([CH3:1])[CH:10]=[CH:9][CH:8]=2)=[O:13])#[N:15]

Participants

4

Reactant 2

HCID 97249Benzonitrile, 3-(bromomethyl)-HCID 39260874-Methyl-1H-indole-2-carboxylic acid

Product 1

HCID 541725614-methyl-1H-indole-2-carboxylic acid 3-cyano-benzyl esterYield 75%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The starting material was 4-methyl-1H-indole-2-carboxylic acid. Alkylation with 3-cyano-benzylbromide (analogously to example 19/1, but the solvent was dimethylformamide instead of tetrahydrofuran) gave 4-methyl-1H-indole-2-carboxylic acid 3-cyano-benzyl ester. Yield: 75%. MS: 291.1 (M+H+).

Sources & evidence

ORD record
ord-8868bb227729428eaf0f9d2d4cf383d6
Source dataset
uspto-grants-2002_01
Patent number
US06337344B1

Reaction notes

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