Cesium carbonate → 3-Bromo-2-methyl-4-(4-trifluoromethyl-benzyl)-4h-thieno[3,2-b]pyrrole-5-carboxylic acid methyl ester

HRID 1951640Notes

Reaction equation

HRID 1951640 reaction equation
[CH3:1][O:2][C:3]([C:5]1[NH:9][C:8]2[C:10]([Br:14])=[C:11]([CH3:13])[S:12][C:7]=2[CH:6]=1)=[O:4].[F:15][C:16]([F:26])([F:25])[C:17]1[CH:24]=[CH:23][C:20]([CH2:21]Br)=[CH:19][CH:18]=1.C([O-])([O-])=O.[Cs+].[Cs+]>CCCCCC.CCOC(C)=O>[CH3:1][O:2][C:3]([C:5]1[N:9]([CH2:21][C:20]2[CH:19]=[CH:18][C:17]([C:16]([F:15])([F:25])[F:26])=[CH:24][CH:23]=2)[C:8]2[C:10]([Br:14])=[C:11]([CH3:13])[S:12][C:7]=2[CH:6]=1)=[O:4]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 1230621-(Bromomethyl)-4-(trifluoromethyl)benzeneHCID 12025193methyl 3-bromo-2-methyl-4H-thieno[3,2-b]pyrrole-5-carboxylate

Product 1

HCID 582977113-Bromo-2-methyl-4-(4-trifluoromethyl-benzyl)-4h-thieno[3,2-b]pyrrole-5-carboxylic acid methyl esterYield 114.6%

Reagents, catalysts & solvents 1

HCID 21226206Ethyl acetate hexaneSolvent

Procedure

A solution of 3-bromo-2-methyl-4H-thieno[3,2-b]pyrrole-5-carboxylic acid methyl ester (8.3 g), 4-trifluoromethybenzyl bromide (8.4 g) and Cs2CO3 (25 g) was stirred for 14 h at room temperature. The reaction mixture was then diluted with 200 ml of 1:1 hexane/EtOAc and filtered through a pad of silica gel. The filtrate was concentrated to give 15 g of the crude title compound which was used for the next step without further purification.

Workup

  1. filtrationfiltered through a pad of silica gel
  2. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-05175622692d4f40a0188c3b31a87abb
Source dataset
uspto-grants-2013_03
Patent number
US08404736B2

Reaction notes

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