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

HRID 930937Notes

Reaction equation

HRID 930937 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 311d (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 (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 (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customPurification by chromatography (silica gel, 0-5% methanol in dichloromethane)

Sources & evidence

ORD record
ord-1af10c3dd74a437281b0754ccb8363ff
Source dataset
uspto-grants-2016_03
Patent number
US09296741B2

Reaction notes

Loading…