Water → 1-(3-Bromo-4-fluoro-phenyl)-2-(1-ethyl-5-methanesulfonyl-1H-pyrrol-3-yl)-ethane-1,2-dione

HRID 646255Notes

Reaction equation

HRID 646255 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:9]#[C:10][C:11]2[CH:12]=[C:13]([S:18]([CH3:21])(=[O:20])=[O:19])[N:14]([CH2:16][CH3:17])[CH:15]=2)[CH:5]=[CH:6][C:7]=1[F:8].C([O-])(O)=[O:23].[Na+].[O-]S([O-])(=O)=O.[Mg+2].[O-][Mn](=O)(=O)=O.[K+].[OH2:39]>CC(C)=O>[Br:1][C:2]1[CH:3]=[C:4]([C:9](=[O:23])[C:10]([C:11]2[CH:12]=[C:13]([S:18]([CH3:21])(=[O:20])=[O:19])[N:14]([CH2:16][CH3:17])[CH:15]=2)=[O:39])[CH:5]=[CH:6][C:7]=1[F:8]

Participants

7

Reactant 5

HCID 962WaterHCID 24083Sulfuric acid magnesium salt (1:1)HCID 516875Potassium PermanganateHCID 516892Sodium BicarbonateHCID 597727414-(3-Bromo-4-fluoro-phenylethynyl)-1-ethyl-2-methanesulfonyl-1H-pyrrole

Product 1

HCID 597726991-(3-Bromo-4-fluoro-phenyl)-2-(1-ethyl-5-methanesulfonyl-1H-pyrrol-3-yl)-ethane-1,2-dioneYield 86%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A solution of 4-(3-bromo-4-fluoro-phenylethynyl)-1-ethyl-2-methanesulfonyl-1H-pyrrole (0.35 g, 0.93 mmol) in acetone was treated with NaHCO3 (0.047 g, 0.56 mmol) and MgSO4 (0.17 g, 1.4 mmol), treated with KMnO4 (0.32 g, 2.05 mmol) and water, stirred at room temperature for 2 h and fitered. The filtercake was washed with EtOAC, dried overnight and washed with EtOAc a second time. The combined filtrates were washed with H2O and brine, dried (Na2SO4) and concentrated in vacuo to yield 0.32 gm (86% yield) of an oil. This was used as is in Step 5.

Workup

  1. washThe filtercake was washed with EtOAC
  2. customdried overnight
  3. washwashed with EtOAc a second time
  4. washThe combined filtrates were washed with H2O and brine
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-09b926405b6840a690738b191732d0c2
Source dataset
uspto-grants-2010_04
Patent number
US07705030B2

Reaction notes

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