4-Bromo-2-butenoic acid → Indole-2-carboxylic acid

HRID 353240Notes

Reaction equation

HRID 353240 reaction equation
Br[CH2:2][CH:3]=[CH:4][C:5]([OH:7])=[O:6].C([CH2:11][CH2:12][CH2:13][CH2:14][C:15]1[NH:16]C2C(C=1)=CC=CC=2)(O)=O.CC(CCCC(Cl)=O)C(Cl)=O>>[C:5]([C:4]1[NH:16][C:15]2[C:2]([CH:3]=1)=[CH:11][CH:12]=[CH:13][CH:14]=2)([OH:7])=[O:6]

Participants

4

Reactant 3

HCID 841404-Bromo-2-butenoic acidHCID 187616392-(4-Carboxy-n-butyl)indoleHCID 225609792-Methylhexanedioyl dichloride

Product 1

HCID 72899Indole-2-carboxylic acid

Procedure

Refer to 32(a) using 4-bromo-2-butenoic acid as the alkylating agent. Preparation of 2-(4-carboxy-n-butyl) indole: Refer to Example 3 using methyl adipyl chloride as the acid chloride. The methyl ester was hydrolyzed in the cyclization workup to provide the product carboxyindole. In the alternative, refer to Example 32b) using 2-(4-carboxy-3-buten-1-yl) indole as the starting material.

Sources & evidence

ORD record
ord-8b14d6ab190d44cd99a3d23791482055
Source dataset
uspto-grants-2004_06
Patent number
US06750240B2

Reaction notes

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