Water → HCID 66906955, compound

HRID 1691830Notes

Reaction equation

HRID 1691830 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([Cl:8])[C:5]([S:9][CH3:10])=[CH:4][C:3]=1[NH:11][C:12]([N:14]1[CH:19]=[CH:18][C:17](=[O:20])[CH2:16][CH:15]1[C:21]1[CH:26]=[CH:25][C:24]([F:27])=[CH:23][CH:22]=1)=[O:13].[OH:28]OS([O-])=O.[K+].[OH2:34]>CO.C(#N)C>[Br:1][C:2]1[CH:7]=[C:6]([Cl:8])[C:5]([S:9]([CH3:10])(=[O:28])=[O:34])=[CH:4][C:3]=1[NH:11][C:12]([N:14]1[CH:19]=[CH:18][C:17](=[O:20])[CH2:16][CH:15]1[C:21]1[CH:22]=[CH:23][C:24]([F:27])=[CH:25][CH:26]=1)=[O:13]

Participants

6

Reactant 3

HCID 962Water2×HCID 23707502Potassium hydroxy sulfiteHCID 66907861HCID 66907861, compound

Product 1

HCID 66906955HCID 66906955, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6342AcetonitrileSolvent

Procedure

To a solution of 2-(4-fluoro-phenyl)-4-oxo-3,4-dihydro-2H-pyridine-1-carboxylic acid (2-bromo-4-chloro-5-methylsulfanyl-phenyl)-amide (0.050 g, 0.106 mmol) in methanol (2 ml) and acetonitrile (2 ml) was added oxone (0.131 g, 0.213 mmol) and water (0.3 ml). The mixture was stirred at room temperature for two hours. Water was added and the mixture was extracted with EtOAc. The organic extract was washed with water and brine, dried over MgSO4, filtered and concentrated to dryness under reduced pressure. Purification of the residue by flash chromatography (EtOAc) gave 2-(4-fluoro-phenyl)-4-oxo-3,4-dihydro-2H-pyridine-1-carboxylic acid (2-bromo-4-chloro-5-methanesulfonyl-phenyl)-amide (0.009 g) as a white foam. MS (M+H) 502.

Workup

  1. extractionthe mixture was extracted with EtOAc
  2. extractionThe organic extract
  3. washwas washed with water and brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated to dryness under reduced pressure
  7. customPurification of the residue by flash chromatography (EtOAc)

Sources & evidence

ORD record
ord-5936e5a86c03452282f79cbe02094add
Source dataset
uspto-grants-2012_04
Patent number
US08153809B2

Reaction notes

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