Methanol → HCID 23114651, compound

HRID 748754Notes

Reaction equation

HRID 748754 reaction equation
CO.[Cl:3][C:4]1[CH:5]=[CH:6][C:7]([S:10][CH:11]([C:18]2[CH:23]=[C:22]([F:24])[CH:21]=[CH:20][C:19]=2[F:25])[C:12]2[CH:17]=[CH:16][N:15]=[CH:14][CH:13]=2)=[N:8][CH:9]=1.[OH2:26].[OH:27]OS([O-])=O.[K+]>ClCCl>[Cl:3][C:4]1[CH:5]=[CH:6][C:7]([S:10]([CH:11]([C:18]2[CH:23]=[C:22]([F:24])[CH:21]=[CH:20][C:19]=2[F:25])[C:12]2[CH:13]=[CH:14][N:15]=[CH:16][CH:17]=2)(=[O:27])=[O:26])=[N:8][CH:9]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 962WaterHCID 23114725HCID 23114725, compoundHCID 23707502Potassium hydroxy sulfite

Product 1

HCID 23114651HCID 23114651, compoundYield 26%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a methanol (6 ml) solution of 5-chloro-2-[(2,5-difluorophenyl-4-pyridylmethyl)thio]pyridine (239 mg, 0.68 mmol) was added a water (12 ml) solution of Oxone (potassium peroxymonosulfate compound, 2 KHSO5.KHSO4.K2SO4) (631 mg, 1.03 mmol) at 0° C. After stirring at room temperature for 3 days, to the reaction mixture was added dichloromethane and the mixture was washed with a saturated aqueous solution of sodium bicarbonate. The organic layer was dried over anhydrous sodium sulfate. After filtration, the filtrate was concentrated under reduced pressure. The residue was purified by preparative high performance liquid chromatography (using a mixed solvent of water/acetonitrile/formic acid). The resulting solid was washed with hexane/diisopropyl ether and then, collected by filtration, whereby the title compound (67 mg, 0.18 mmol, 26%) was obtained as a white powder.

Workup

  1. washthe mixture was washed with a saturated aqueous solution of sodium bicarbonate
  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 residue was purified by preparative high performance liquid chromatography (
  6. washThe resulting solid was washed with hexane/diisopropyl ether

Sources & evidence

ORD record
ord-6fd8a279724e4323ab00da5159fe9128
Source dataset
uspto-grants-2008_07
Patent number
US07399775B2

Reaction notes

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