Water → HCID 59576358, compound

HRID 2069513Notes

Reaction equation

HRID 2069513 reaction equation
[CH3:1][O:2][C:3]([C:5]1[NH:6][CH:7]=[C:8]([C:10](=[O:14])[CH:11]([CH3:13])[CH3:12])[CH:9]=1)=[O:4].C(=O)([O-])[O-].[Cs+].[Cs+].Br[CH2:22][C:23]1[CH:28]=[CH:27][C:26]([F:29])=[C:25]([F:30])[CH:24]=1.O>CN(C=O)C>[CH3:1][O:2][C:3]([C:5]1[N:6]([CH2:22][C:23]2[CH:28]=[CH:27][C:26]([F:29])=[C:25]([F:30])[CH:24]=2)[CH:7]=[C:8]([C:10](=[O:14])[CH:11]([CH3:12])[CH3:13])[CH:9]=1)=[O:4]

Participants

6

Reactant 4

HCID 962WaterHCID 10796Cesium carbonateHCID 5814364-(Bromomethyl)-1,2-difluorobenzeneHCID 59576364HCID 59576364, compound

Product 1

HCID 59576358HCID 59576358, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of 4-isobutyryl-1H-pyrrole-2-carboxylic acid methyl ester (B1-I) and cesium carbonate were stirred in dry DMF for 10 minutes at 40-50° C. To it 1-bromomethyl-3,4-difluorobenzene was added and the reaction was stirred for 18 hrs at 50° C. Water was added to the reaction and extracted with ethyl acetate. The organic layer was washed with brine and dried over anhydrous sodium sulfate. The solvent was evaporated to obtain 1-(3,4-difluoro-benzyl)-4-isobutyryl-1H-pyrrole-2-carboxylic acid methyl ester (B1-II).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe solvent was evaporated

Sources & evidence

ORD record
ord-b8805788970040cca03560810d409a58
Source dataset
uspto-grants-2012_10
Patent number
US08299115B2

Reaction notes

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