Methanol → 3-Bromo-2-(2,4-difluorophenoxy)-5-(methylsulfonylmethyl)pyridine

HRID 633558Notes

Reaction equation

HRID 633558 reaction equation
[Br:1][C:2]1[C:3]([O:11][C:12]2[CH:17]=[CH:16][C:15]([F:18])=[CH:14][C:13]=2[F:19])=[N:4][CH:5]=[C:6]([CH2:8]SC)[CH:7]=1.O[O:21][S:22]([O-:24])=O.[K+].[CH3:26]O>O>[Br:1][C:2]1[C:3]([O:11][C:12]2[CH:17]=[CH:16][C:15]([F:18])=[CH:14][C:13]=2[F:19])=[N:4][CH:5]=[C:6]([CH2:8][S:22]([CH3:26])(=[O:24])=[O:21])[CH:7]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 23707502Potassium hydroxy sulfiteHCID 867210773-Bromo-2-(2,4-difluorophenoxy)-5-(methylthiomethyl)pyridine

Product 1

HCID 867210783-Bromo-2-(2,4-difluorophenoxy)-5-(methylsulfonylmethyl)pyridineYield 60%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of the product from Example 60D (0.66 g, 1.906 mmol) at 0° C. in methanol (7.33 mL) was treated with a solution of Oxone (2.461 g, 4.00 mmol) in water (7.33 mL), stirred at ambient temperature for two hours and partitioned between ethyl acetate and water. The organic layer was washed with saturated aqueous sodium chloride, dried (anhydrous Na2SO4), filtered, and concentrated. Purification by chromatography (silica gel, 0-5% methanol in dichloromethane) afforded the title compound (0.433 g, 60%).

Workup

  1. custompartitioned between ethyl acetate and water
  2. washThe organic layer was washed with saturated aqueous sodium chloride
  3. dry with materialdried (anhydrous Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customPurification by chromatography (silica gel, 0-5% methanol in dichloromethane)

Sources & evidence

ORD record
ord-4bf384b6b4a646f884d5b7218cc4ff56
Source dataset
uspto-grants-2016_04
Patent number
US09321764B2

Reaction notes

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