Bromine → 1H-Indole-6-carboxylic acid, 2-bromo-3-cyclopentyl-1-methyl-, 1-methylethyl ester

HRID 1907888Notes

Reaction equation

[Br:1][C:2]1[N:3]([CH3:19])[C:4]2[C:9]([C:10]=1[CH:11]1[CH2:15][CH2:14][CH2:13][CH2:12]1)=[CH:8][CH:7]=[C:6]([C:16]([O-:18])=[O:17])[CH:5]=2.[CH:20]1(C2C3C(=CC(C([O-])=O)=CC=3)N(C)C=2)[CH2:24]CC[CH2:21]1.BrBr>>[Br:1][C:2]1[N:3]([CH3:19])[C:4]2[C:9]([C:10]=1[CH:11]1[CH2:15][CH2:14][CH2:13][CH2:12]1)=[CH:8][CH:7]=[C:6]([C:16]([O:18][CH:20]([CH3:24])[CH3:21])=[O:17])[CH:5]=2

Participants

Reactant 3

HCID 24408Bromine

HCID 86665159HCID 86665159, compound

HCID 86665160HCID 86665160, compound

Product 1

HCID 668358531H-Indole-6-carboxylic acid, 2-bromo-3-cyclopentyl-1-methyl-, 1-methylethyl ester

Procedure

This process identified the optimal conditions for the synthesis of 2-bromo-3-cyclopentyl-1-methyl-1H-indole-6-carboxylate via bromination of the corresponding 3-cyclopentyl-1-methyl-1H-indole-6-carboxylate with bromine. It's very important to control the reaction temperature and to quench the reaction mixture with a mixture of aqueous sodium thiosulfate and 4-methylmorpholine to minimize the formation of the dibromo- and 2-indolone impurities. Further neutralization of the crude product with NaOH in isopropanol greatly increases the stability of the isolated product.

Workup

customto quench the reaction mixture
additionwith a mixture of aqueous sodium thiosulfate and 4-methylmorpholine
temperatureFurther neutralization of the crude product with NaOH in isopropanol greatly increases the stability of the isolated product

Sources & evidence

ORD record: ord-444b4350289a439a9d619eefeca1ad9d
Source dataset: uspto-grants-2013_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08598183B2

Reaction notes

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