Tetrahydrofuran → 4-Chloro-5,7-difluoro-3-methyl-2-(5-(methylsulfonyl)pyridin-3-yl)quinoline

HRID 1618693Notes

Reaction equation

HRID 1618693 reaction equation
[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([F:13])=[CH:9][C:10]=2[F:12])[N:5]=[C:4]([C:14]2[CH:15]=[N:16][CH:17]=[C:18](SC)[CH:19]=2)[C:3]=1[CH3:22].O[O:24][S:25]([O-:27])=O.[K+].[CH2:29]1COCC1>O.CCOC(C)=O>[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([F:13])=[CH:9][C:10]=2[F:12])[N:5]=[C:4]([C:14]2[CH:15]=[N:16][CH:17]=[C:18]([S:25]([CH3:29])(=[O:27])=[O:24])[CH:19]=2)[C:3]=1[CH3:22]

Participants

6

Reactant 3

HCID 8028TetrahydrofuranHCID 23707502Potassium hydroxy sulfiteHCID 596312844-Chloro-5,7-difluoro-3-methyl-2-(5-(methylthio)pyridin-3-yl)quinoline

Product 1

HCID 672857114-Chloro-5,7-difluoro-3-methyl-2-(5-(methylsulfonyl)pyridin-3-yl)quinoline

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a stirring suspension of 4-chloro-5,7-difluoro-3-methyl-2-(5-(methylthio)pyridin-3-yl)quinoline (200 mg, 0.594 mmol) in THF (4.5 mL) and water (1.5 mL) was added oxone (913 mg, 1.485 mmol). The reaction was stirred at rt for 18 h, then poured into 15 mL water and stirred for 10 min. The resulting precipitate was isolated by filtration, then dissolved in EtOAc, dried over MgSO4, and concentrated under reduced pressure to give 4-chloro-5,7-difluoro-3-methyl-2-(5-(methylsulfonyl)pyridin-3-yl)quinoline. Mass Spectrum (ESI) m/e=369.0 (M+1).

Workup

  1. stirringstirred for 10 min
  2. customThe resulting precipitate was isolated by filtration
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-ee86bd05642e4fd9ac9b0fddfe7a0cf2
Source dataset
uspto-grants-2014_07
Patent number
US08765940B2

Reaction notes

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