Cesium carbonate → 4-bromo-1-[(5-chloro-pyridin-2-ylcarbamoyl)-methyl]-3,5-dimethyl-1H-pyrrole-2-carboxylic acid ethyl ester

HRID 2375809Notes

Reaction equation

HRID 2375809 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[NH:7][C:8]([CH3:13])=[C:9]([Br:12])[C:10]=1[CH3:11])=[O:5])[CH3:2].C([O-])([O-])=O.[Cs+].[Cs+].Br[CH2:21][C:22]([NH:24][C:25]1[CH:30]=[CH:29][C:28]([Cl:31])=[CH:27][N:26]=1)=[O:23]>CN(C=O)C>[CH2:1]([O:3][C:4]([C:6]1[N:7]([CH2:21][C:22](=[O:23])[NH:24][C:25]2[CH:30]=[CH:29][C:28]([Cl:31])=[CH:27][N:26]=2)[C:8]([CH3:13])=[C:9]([Br:12])[C:10]=1[CH3:11])=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 138486ethyl 4-bromo-3,5-dimethyl-1H-pyrrole-2-carboxylateHCID 34211102-Bromo-N-(5-chloro-2-pyridinyl)acetamide

Product 1

HCID 692894104-bromo-1-[(5-chloro-pyridin-2-ylcarbamoyl)-methyl]-3,5-dimethyl-1H-pyrrole-2-carboxylic acid ethyl esterYield 26.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-bromo-3,5-dimethyl-1H-pyrrole-2-carboxylic acid ethyl ester (492 mg) in DMF (5 mL) was added Cs2CO3 (912 mg). The mixture was stirred for 30 min at RT after which 2-bromo-N-(5-chloro-pyridin-2-yl)-acetamide (499 mg) was added. Stirring was continued for 2 h at RT whereupon the mixture was filtered and concentrated. The residue was subjected to preparative HPLC(CH3CN/H2O gradient+0.05% TFA) to give 4-bromo-1-[(5-chloro-pyridin-2-ylcarbamoyl)-methyl]-3,5-dimethyl-1H-pyrrole-2-carboxylic acid ethyl ester (220 mg).

Workup

  1. additionwas added
  2. filtrationwas filtered
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-83bb7b9a59a24d1e969404f442c1a33a
Source dataset
uspto-grants-2008_12
Patent number
US07465806B2

Reaction notes

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