Ethyl (2Z)-2-azido-3-(4-bromophenyl)-2-propenoate → 6-Bromo-1H-indole-2-carboxylic acid ethyl ester

HRID 1169354Notes

Reaction equation

HRID 1169354 reaction equation
[N:1](/[C:4](=[CH:10]\[C:11]1[CH:16]=[CH:15][C:14]([Br:17])=[CH:13][CH:12]=1)/[C:5]([O:7][CH2:8][CH3:9])=[O:6])=[N+]=[N-]>C1(C)C(C)=CC=CC=1>[Br:17][C:14]1[CH:15]=[C:16]2[C:11]([CH:10]=[C:4]([C:5]([O:7][CH2:8][CH3:9])=[O:6])[NH:1]2)=[CH:12][CH:13]=1

Participants

3

Reactant 1

HCID 24767341Ethyl (2Z)-2-azido-3-(4-bromophenyl)-2-propenoate

Product 1

HCID 70094966-Bromo-1H-indole-2-carboxylic acid ethyl esterYield 56.8%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

A solution of ethyl (Z)-2-azido-3-(4-bromophenyl)acrylate (6.24 g) in xylene (200 ml) was heated at reflux for 4 hours. After cooling to room temperature, the reaction mixture was concentrated under reduced pressure, and the precipitated crystals were collected by filtration. The crystals were washed with xylene and hexane to obtain ethyl 6-bromo-1H-indole-2-carboxylate (3.21 g) as colorless crystals.

Workup

  1. temperatureat reflux for 4 hours
  2. concentrationthe reaction mixture was concentrated under reduced pressure
  3. filtrationthe precipitated crystals were collected by filtration
  4. washThe crystals were washed with xylene and hexane

Sources & evidence

ORD record
ord-0b5e2b68f9d14c03beea8a4f5dfe1165
Source dataset
uspto-grants-2003_09
Patent number
US06627651B1

Reaction notes

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