Methanol → 5-Chloro-2-[[1-(2,5-difluorophenyl)-5-(methylsulfonyl)pentyl]sulfonyl]pyridine

HRID 748749Notes

Reaction equation

HRID 748749 reaction equation
CO.[Cl:3][C:4]1[CH:5]=[CH:6][C:7]([S:10][CH:11]([C:20]2[CH:25]=[C:24]([F:26])[CH:23]=[CH:22][C:21]=2[F:27])[CH2:12][CH2:13][CH2:14][CH2:15][S:16]([CH3:19])(=[O:18])=[O:17])=[N:8][CH:9]=1.[OH2:28].[OH:29]OS([O-])=O.[K+]>C(OCC)(=O)C.ClCCl>[Cl:3][C:4]1[CH:5]=[CH:6][C:7]([S:10]([CH:11]([C:20]2[CH:25]=[C:24]([F:26])[CH:23]=[CH:22][C:21]=2[F:27])[CH2:12][CH2:13][CH2:14][CH2:15][S:16]([CH3:19])(=[O:18])=[O:17])(=[O:29])=[O:28])=[N:8][CH:9]=1

Participants

7

Reactant 4

HCID 887MethanolHCID 962WaterHCID 23707502Potassium hydroxy sulfiteHCID 597507325-Chloro-2-[[1-(2,5-difluorophenyl)-5-(methylsulfonyl)pentyl]thio]pyridine

Product 1

HCID 597508135-Chloro-2-[[1-(2,5-difluorophenyl)-5-(methylsulfonyl)pentyl]sulfonyl]pyridineYield 56%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a methanol (2 ml) solution of 5-chloro-2-[[1-(2,5-difluorophenyl)-5-(methylsulfonyl)pentyl]thio]pyridine (100 mg, 0.25 mmol) was added a water (2 ml) solution of Oxone (potassium peroxymonosulfate compound, 2 KHSO5.KHSO4.K2SO4) (303 mg, 0.49 mmol) at 0° C. After shaking at room temperature for 22 hours, the reaction mixture was added with dichloromethane and the mixture was washed with water. The organic layer was dried over anhydrous sodium sulfate. After filtration, the filtrate was concentrated under reduced pressure. The residue was subjected to flash chromatography on a silica gel column, and the fraction obtained from the hexane:ethyl acetate=1:1 eluate was concentrated under reduced pressure, whereby the title compound (61 mg, 0.14 mmol, 56%) was obtained as a colorless foam.

Workup

  1. washthe mixture was washed with water
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. filtrationAfter filtration
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. customthe fraction obtained from the hexane

Sources & evidence

ORD record
ord-234f119d69484ddfad51e7c83ef31cd8
Source dataset
uspto-grants-2008_07
Patent number
US07399775B2

Reaction notes

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