HCID 66697772, compound → HCID 86664253, compound

HRID 340593Notes

Reaction equation

HRID 340593 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([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:4][CH:3]=1>C1(C)C=CC=CC=1.[O-2].[O-2].[Mn+4]>[F:1][C:2]1[CH:7]=[CH:6][C:5]([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:4][CH:3]=1

Participants

4

Reactant 1

HCID 66697772HCID 66697772, compound

Product 1

HCID 86664253HCID 86664253, compoundYield 80.5%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

{5-[(4-Fluorophenyl)sulfonyl]-1-(2-fluoropyridin-3-yl)-1H-pyrazol-3-yl}methanol (135 mg) was dissolved in toluene (2 mL), manganese dioxide (167 mg) was added, and the mixture was stirred at 100° C. for 42 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 oil (yield 108 mg, yield 80%).

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-bfd0386b97534bb983a40726d84693e9
Source dataset
uspto-grants-2014_11
Patent number
US08895588B2

Reaction notes

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