Methanol → HCID 23114651, compound

HRID 2080389Notes

Reaction equation

HRID 2080389 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 peroxomonosulfate compound, 2KHSO5.KHSO4.K2SO4) (631 mg, 1.03 mmol) at 0° C. After the reaction mixture was stirred at room temperature for 3 days, dichloromethane was added thereto. The resulting mixture was washed with a saturated aqueous solution of sodium bicarbonate. The organic layer was dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated under reduced pressure. The residue was purified by preparative high performance liquid chromatography (using a mixed solvent system of water/acetonitrile/formic acid). The solid thus obtained was washed with hexane/diisopropyl ether and then collected by filtration to give the title compound (67 mg, 0.18 mmol, 26%) as a white powder.

Workup

  1. washThe resulting mixture was washed with a saturated aqueous solution of sodium bicarbonate
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated under reduced pressure
  5. customThe residue was purified by preparative high performance liquid chromatography (
  6. customThe solid thus obtained
  7. washwas washed with hexane/diisopropyl ether
  8. filtrationcollected by filtration

Sources & evidence

ORD record
ord-28f5d8c77cdb4e3fae49f610933ac764
Source dataset
uspto-grants-2011_04
Patent number
US07932271B2

Reaction notes

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