HCID 66697777, compound → HCID 86664255, compound

HRID 340601Notes

Reaction equation

HRID 340601 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([S:8]([C:11]2[N:15]([C:16]3[C:17]([F:22])=[N:18][CH:19]=[CH:20][CH:21]=3)[N:14]=[C:13]([CH2:23][OH:24])[CH:12]=2)(=[O:10])=[O:9])[CH:5]=[CH:6][CH:7]=1>C1(C)C=CC=CC=1.[O-2].[O-2].[Mn+4]>[Br:1][C:2]1[CH:3]=[C:4]([S:8]([C:11]2[N:15]([C:16]3[C:17]([F:22])=[N:18][CH:19]=[CH:20][CH:21]=3)[N:14]=[C:13]([CH:23]=[O:24])[CH:12]=2)(=[O:9])=[O:10])[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 1

HCID 66697777HCID 66697777, compound

Product 1

HCID 86664255HCID 86664255, compoundYield 76%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 1140TolueneSolvent

Conditions

Temperature
90 °C

Procedure

{5-[(3-Bromophenyl)sulfonyl]-1-(2-fluoropyridin-3-yl)-1H-pyrazol-3-yl}methanol (371 mg) was dissolved in toluene (5 mL), manganese dioxide (626 mg) was added and the mixture was stirred at 90° C. for 5 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=19:1→3:1) to give the title compound as a colorless solid (yield 280 mg, yield 76%).

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=19:1→3:1)

Sources & evidence

ORD record
ord-09931de0ced341f2a099867164e97062
Source dataset
uspto-grants-2014_11
Patent number
US08895588B2

Reaction notes

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