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

HRID 1431598Notes

Reaction equation

HRID 1431598 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 (4.4 mL) and water (1.4 mL) was added oxone (913 mg, 1.49 mmol). The reaction was stirred at rt for 18 h, then poured into 15 mL water and stirred for ten min. The resulting precipitate was isolated by filtration, then dissolved in EtOAc, dried over magnesium sulfate, and cond, affording 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 ten min
  2. customThe resulting precipitate was isolated by filtration
  3. dry with materialdried over magnesium sulfate, and cond

Sources & evidence

ORD record
ord-b063933084ff4d108ff5cf161cd6dfb0
Source dataset
uspto-grants-2015_01
Patent number
US08940724B2

Reaction notes

Loading…