Ethyl 2-azido-3-(5-bromothiophen-2-yl)acrylate → ethyl 2-bromo-4H-thieno[3,2-b]pyrrole-5-carboxylate

HRID 77433

Reaction equation

HRID 77433 reaction equation
[N:1]([C:4](=[CH:10][C:11]1[S:12][C:13]([Br:16])=[CH:14][CH:15]=1)[C:5]([O:7][CH2:8][CH3:9])=[O:6])=[N+]=[N-]>CC1C=CC=CC=1C>[Br:16][C:13]1[S:12][C:11]2[CH:10]=[C:4]([C:5]([O:7][CH2:8][CH3:9])=[O:6])[NH:1][C:15]=2[CH:14]=1

Participants

3

Reactant 1

HCID 73166977Ethyl 2-azido-3-(5-bromothiophen-2-yl)acrylate

Product 1

HCID 13164349ethyl 2-bromo-4H-thieno[3,2-b]pyrrole-5-carboxylateYield 82%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

Acrylate 60 (3.81 g, 12.6 mmol) in o-xylene was refluxed for 20 min. After removing the o-xylene, the crude product was purified by column chromatography (EtOAc/Hexane: 1/10) to give carboxylate 61 (2.83 g, 82%) as a white solid.

Workup

  1. customAfter removing the o-xylene
  2. customthe crude product was purified by column chromatography (EtOAc/Hexane: 1/10)

Sources & evidence

ORD record
ord-5f4536bbbabf40fe8757e28a2bdfa0eb
Source dataset
uspto-grants-2014_09
Patent number
US08841305B2

Linked notes

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