(1-Methyl-1H-imidazol-5-yl)(2-(trifluoromethyl)pyridin-4-yl)methanol → (1-Methyl-1H-imidazol-5-yl)(2-(trifluoromethyl)pyridin-4-yl)methanone

HRID 926490Notes

Reaction equation

HRID 926490 reaction equation
[CH3:1][N:2]1[C:6]([CH:7]([C:9]2[CH:14]=[CH:13][N:12]=[C:11]([C:15]([F:18])([F:17])[F:16])[CH:10]=2)[OH:8])=[CH:5][N:4]=[CH:3]1>O1CCOCC1.[O-2].[O-2].[Mn+4]>[CH3:1][N:2]1[C:6]([C:7]([C:9]2[CH:14]=[CH:13][N:12]=[C:11]([C:15]([F:18])([F:16])[F:17])[CH:10]=2)=[O:8])=[CH:5][N:4]=[CH:3]1

Participants

4

Reactant 1

HCID 86715639(1-Methyl-1H-imidazol-5-yl)(2-(trifluoromethyl)pyridin-4-yl)methanol

Product 1

HCID 86715640(1-Methyl-1H-imidazol-5-yl)(2-(trifluoromethyl)pyridin-4-yl)methanone

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 312751,4-DioxaneSolvent

Procedure

A heterogeneous mixture of (1-methyl-1H-imidazol-5-yl)(2-(trifluoromethyl)pyridin-4-yl)methanol (0.300 g, 1.16 mmol, Intermediate 27: step a) and manganese dioxide (0.506 g, 5.83 mmol) in 1,4-dioxane (12 mL) was stirred at 100° C. for 1 hour. The reaction mixture was then cooled to room temperature, filtered through Celite®, washed with EtOAc, and concentrated. The organic phase was dried (MgSO4), filtered, and concentrated. The crude product was purified by flash column chromatography (silica gel, 0-100% EtOAc-DCM) to provide the title compound as a white solid.

Workup

  1. filtrationfiltered through Celite®
  2. washwashed with EtOAc
  3. concentrationconcentrated
  4. dry with materialThe organic phase was dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude product was purified by flash column chromatography (silica gel, 0-100% EtOAc-DCM)

Sources & evidence

ORD record
ord-8e791b122d0d4e149b7af2cd8a34b4c9
Source dataset
uspto-grants-2016_03
Patent number
US09284308B2

Reaction notes

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