m-Chloroperbenzoic acid → 5-[[(4-Fluorophenyl)sulfonyl](2,3,6-trifluorophenyl)methyl]-4-methylpyridine-2-carboxamide

HRID 1641703Notes

Reaction equation

HRID 1641703 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([CH:10]([C:21]2[C:26]([F:27])=[CH:25][CH:24]=[C:23]([F:28])[C:22]=2[F:29])[C:11]2[C:12]([CH3:20])=[CH:13][C:14]([C:17]([NH2:19])=[O:18])=[N:15][CH:16]=2)=[O:9])=[CH:4][CH:3]=1.ClC1C=CC=C(C(OO)=[O:38])C=1>C(Cl)Cl>[F:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([CH:10]([C:21]2[C:26]([F:27])=[CH:25][CH:24]=[C:23]([F:28])[C:22]=2[F:29])[C:11]2[C:12]([CH3:20])=[CH:13][C:14]([C:17]([NH2:19])=[O:18])=[N:15][CH:16]=2)(=[O:38])=[O:9])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 57736544HCID 57736544, compound

Product 1

HCID 577365415-[[(4-Fluorophenyl)sulfonyl](2,3,6-trifluorophenyl)methyl]-4-methylpyridine-2-carboxamideYield 61%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 5-[[(4-fluorophenyl)sulfinyl](2,3,6-trifluorophenyl)methyl]-4-methylpyridine-2-carboxamide (106 mg, 0.25 mmol) in methylene chloride (5 ml), 3-chloroperbenzoic acid (66 mg, 0.25 mmol) was added at 0° C. After stirring for 5 days at room temperature, the reaction mixture was washed with 1 N aqueous sodium hydroxide. The organic layer was dried over anhydrous sodium sulfate and filtered, then the filtrate was concentrated under reduced pressure, and the obtained residue was subjected to preparative thin-layer chromatography (developed with hexane:ethyl acetate=2:3, eluted with methylene chloride:methanol=4:1). The obtained fraction was concentrated under reduced pressure, and the resulting residue was washed with a mixed solvent of ethanol and diethyl ether, and was collected by filtration, to obtain the title compound (67 mg, 0.15 mmol, 61%) as a white solid.

Workup

  1. washthe reaction mixture was washed with 1 N aqueous sodium hydroxide
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. washthin-layer chromatography (developed with hexane:ethyl acetate=2:3, eluted with methylene chloride:methanol=4:1)
  6. concentrationThe obtained fraction was concentrated under reduced pressure
  7. washthe resulting residue was washed with a mixed solvent of ethanol and diethyl ether
  8. filtrationwas collected by filtration

Sources & evidence

ORD record
ord-4644e98ffb2b4848b31e77b6a3e4857c
Source dataset
uspto-grants-2012_02
Patent number
US08114886B2

Reaction notes

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