2-Azido-3-(4-bromo-5-methyl-thiophen-2-yl)-acrylic acid methyl ester → methyl 3-bromo-2-methyl-4H-thieno[3,2-b]pyrrole-5-carboxylate

HRID 1951639Notes

Reaction equation

HRID 1951639 reaction equation
[CH3:1][O:2][C:3](=[O:16])[C:4]([N:13]=[N+]=[N-])=[CH:5][C:6]1[S:7][C:8]([CH3:12])=[C:9]([Br:11])[CH:10]=1>C1(C)C(C)=CC=CC=1>[CH3:1][O:2][C:3]([C:4]1[NH:13][C:10]2[C:9]([Br:11])=[C:8]([CH3:12])[S:7][C:6]=2[CH:5]=1)=[O:16]

Participants

3

Reactant 1

HCID 767450662-Azido-3-(4-bromo-5-methyl-thiophen-2-yl)-acrylic acid methyl ester

Product 1

HCID 12025193methyl 3-bromo-2-methyl-4H-thieno[3,2-b]pyrrole-5-carboxylateYield 76.5%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent2×

Procedure

To a refluxing xylene (100 ml) was added the crude product of Step 2 (18 g) in 250 ml of xylene over a period of 20 min. After refluxing for 10 min, the reaction mixture was cooled and concentrated to volume of about 100 ml. The solid was collected by filtration to give 12.5 g of the title compound as a white solid.

Workup

  1. temperatureAfter refluxing for 10 min
  2. temperaturethe reaction mixture was cooled
  3. concentrationconcentrated to volume of about 100 ml
  4. filtrationThe solid was collected by filtration

Sources & evidence

ORD record
ord-1920b700faca484098975edb2fd6cc41
Source dataset
uspto-grants-2013_03
Patent number
US08404736B2

Reaction notes

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