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

HRID 1618705Notes

Reaction equation

HRID 1618705 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:19]=[CH:18][CH:17]=[CH:16][C:15]=2SC)[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:19]=[CH:18][CH:17]=[CH:16][C:15]=2[S:25]([CH3:29])(=[O:27])=[O:24])[C:3]=1[CH3:22]

Participants

6

Reactant 3

HCID 8028TetrahydrofuranHCID 23707502Potassium hydroxy sulfiteHCID 596313634-Chloro-5,7-difluoro-3-methyl-2-(2-(methylthio)phenyl)quinoline

Product 1

HCID 596310374-Chloro-5,7-difluoro-3-methyl-2-(2-(methylsulfonyl)phenyl)quinoline

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a stirring solution of 4-chloro-5,7-difluoro-3-methyl-2-(2-(methylthio)phenyl)-quinoline (0.940 g, 2.80 mmol) in THF (20 mL) and water (6.7 mL) was added oxone (4.3 g, 7.00 mmol). The reaction was stirred at rt for 2 h, then 75 mL water was added and the mixture was stirred for 10 min. The resulting precipitate was isolated by filtration, then dissolved in EtOAc, dried over MgSO4, and concentrated to give 4-chloro-5,7-difluoro-3-methyl-2-(2-(methylsulfonyl)phenyl)-quinoline. Mass Spectrum (ESI) m/e=368.0 (M+1).

Workup

  1. stirringthe mixture was stirred for 10 min
  2. customThe resulting precipitate was isolated by filtration
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-7c9df8cd4eef4eb39ad1efdc96fc568f
Source dataset
uspto-grants-2014_07
Patent number
US08765940B2

Reaction notes

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