Water → HCID 59576362, compound

HRID 2069515Notes

Reaction equation

HRID 2069515 reaction equation
[CH3:1][O:2][C:3]([C:5]1[NH:6][CH:7]=[C:8]([S:10]([C:13]2[S:14][CH:15]=[CH:16][CH:17]=2)(=[O:12])=[O:11])[CH:9]=1)=[O:4].[F:18][C:19]1[CH:20]=[C:21]([CH:24]=[CH:25][C:26]=1[F:27])[CH2:22]Br.O>CN(C)C=O.C(=O)([O-])[O-].[Cs+].[Cs+]>[CH3:1][O:2][C:3]([C:5]1[N:6]([CH2:22][C:21]2[CH:24]=[CH:25][C:26]([F:27])=[C:19]([F:18])[CH:20]=2)[CH:7]=[C:8]([S:10]([C:13]2[S:14][CH:15]=[CH:16][CH:17]=2)(=[O:11])=[O:12])[CH:9]=1)=[O:4]

Participants

6

Reactant 3

HCID 962WaterHCID 5814364-(Bromomethyl)-1,2-difluorobenzeneHCID 59576359HCID 59576359, compound

Product 1

HCID 59576362HCID 59576362, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 10796Cesium carbonateSolvent

Conditions

Temperature
45 °C

Procedure

To a solution of 4-(thiophene-2-sulfonyl)-1H-pyrrole-2-carboxylic acid methyl ester (D1-I) in dry dimethylformamide, cesium carbonate was added at 40-50° C. To this was added 3,4-difluro benzyl bromide and stirred overnight at 40-50° C. Reaction mixture was taken in to water and extracted with ethyl acetate, organic layer was washed with water and brine, dried over anhydrous sodium sulfate, filtered and concentrated to afford 1-(3,4-difluoro-benzyl)-4-(thiophene-2-sulfonyl)-1H-pyrrole-2-carboxylic acid methyl ester (D1-II).

Workup

  1. customReaction mixture
  2. extractionextracted with ethyl acetate, organic layer
  3. washwas washed with water and brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-490bd75ce3f84caba3cc8d02ac8a4780
Source dataset
uspto-grants-2012_10
Patent number
US08299115B2

Reaction notes

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