N-bromobutanimide → 6-bromo-4H-thieno[3,2-b]pyrrole-5-carboxylic acid

HRID 1363278Notes

Reaction equation

[S:1]1[C:8]2[CH:7]=[C:6]([C:9]([OH:11])=[O:10])[NH:5][C:4]=2[CH:3]=[CH:2]1.[Br:12]N1C(=O)CCC1=O.ClC1C2SC=CC=2NC=1C(O)=O>>[Br:12][C:7]1[C:8]2[S:1][CH:2]=[CH:3][C:4]=2[NH:5][C:6]=1[C:9]([OH:11])=[O:10]

Participants

Reactant 3

HCID 67184N-bromobutanimide

HCID 49612544H-thieno(3,2-b)pyrrole-5-carboxylic acid2×

HCID 248559556-chloro-4H-thieno[3,2-b]pyrrole-5-carboxylic acid

Product 1

HCID 596485386-bromo-4H-thieno[3,2-b]pyrrole-5-carboxylic acidYield 10.5%

Procedure

The title compound was synthesized from 4H-thieno[3,2-b]pyrrole-5-carboxylic acid (0.1 g, 0.60 mmol, 1 equiv) and N-bromosuccinimide (NBS) (0.107 g, 0.599 mmol, 1 equiv) according to the halogenation method reported for the chlorination of 4H-thieno[3,2-b]pyrrole-5-carboxylic acid (with NCS) to 6-chloro-4H-thieno[3,2-b]pyrrole-5-carboxylic acid, providing the desired 6-bromo-4H-thieno[3,2-b]pyrrole-5-carboxylic acid 71 (15.5 mg, 10.5%). LC/MS m/e 243.9 (M−H). tR of product: 2.5-2.8 min. 1H NMR (400 MHz, CD3OD) δ ppm 7.42 (d, J=5.32 Hz, 1H), 7.01 (d, J=5.32 Hz, 1H).

Sources & evidence

ORD record: ord-3d94a794f507434f8cff79702a3e5617
Source dataset: uspto-grants-2011_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07884124B2

Reaction notes

Loading…