HCID 66697803, compound → HCID 86664254, compound

HRID 340598Notes

Reaction equation

HRID 340598 reaction equation
[F:1][C:2]1[C:7]([N:8]2[C:12]([S:13]([C:16]3[CH:21]=[CH:20][CH:19]=[C:18]([CH3:22])[CH:17]=3)(=[O:15])=[O:14])=[CH:11][C:10]([CH2:23][OH:24])=[N:9]2)=[CH:6][CH:5]=[CH:4][N:3]=1>C1(C)C=CC=CC=1.[O-2].[O-2].[Mn+4]>[F:1][C:2]1[C:7]([N:8]2[C:12]([S:13]([C:16]3[CH:21]=[CH:20][CH:19]=[C:18]([CH3:22])[CH:17]=3)(=[O:15])=[O:14])=[CH:11][C:10]([CH:23]=[O:24])=[N:9]2)=[CH:6][CH:5]=[CH:4][N:3]=1

Participants

4

Reactant 1

HCID 66697803HCID 66697803, compound

Product 1

HCID 86664254HCID 86664254, compoundYield 83.6%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 1140TolueneSolvent

Conditions

Temperature
90 °C

Procedure

{1-(2-Fluoropyridin-3-yl)-5-[(3-methylphenyl)sulfonyl]-1H-pyrazol-3-yl}methanol (320 mg) was dissolved in toluene (5 mL), manganese dioxide (802 mg) was added, and the mixture was stirred at 90° C. for 4 hr. The reaction mixture was allowed to cool to room temperature, and filtered through celite. The filtrate was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (eluent:hexane-ethyl acetate=9:1→2:1) to give the title compound as a colorless oil (yield 266 mg, yield 83%).

Workup

  1. temperatureto cool to room temperature
  2. filtrationfiltered through celite
  3. concentrationThe filtrate was concentrated under reduced pressure
  4. customthe residue was purified by silica gel column chromatography (eluent:hexane-ethyl acetate=9:1→2:1)

Sources & evidence

ORD record
ord-df8401c7aa2b41fbaec4b8a3aa8f0dbc
Source dataset
uspto-grants-2014_11
Patent number
US08895588B2

Reaction notes

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