Tetrahydrofuran → 4-Chloro-5,7-difluoro-2-(5-fluoro-2-(methylsulfonyl)phenyl)-3-methylquinoline

HRID 1431623Notes

Reaction equation

HRID 1431623 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]=[C:18]([F:20])[CH:17]=[CH:16][C:15]=2SC)[C:3]=1[CH3:23].O[O:25][S:26]([O-:28])=O.[K+].[CH2:30]1COCC1>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]=[C:18]([F:20])[CH:17]=[CH:16][C:15]=2[S:26]([CH3:30])(=[O:28])=[O:25])[C:3]=1[CH3:23]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 23707502Potassium hydroxy sulfiteHCID 596311784-Chloro-5,7-difluoro-2-(5-fluoro-2-(methylthio)phenyl)-3-methylquinoline

Product 1

HCID 596313454-Chloro-5,7-difluoro-2-(5-fluoro-2-(methylsulfonyl)phenyl)-3-methylquinoline

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

The 4-chloro-5,7-difluoro-2-(5-fluoro-2-(methylthio)phenyl)-3-methylquinoline (320 mg, 0.90 mmol) was dissolved in a mixture of THF (6.7 mL) and water (2.2 mL). To the solution was added Oxone™ (1.40 g, 2.2 mmol) and the resulting slurry was stirred vigorously for 16 h. The reaction mixture was added to 25 mL of water and stirred vigorously for 10 min and then filtered. The precipitate was dissolved in EtOAc and then dried over magnesium sulfate. The filtrate was cond to give 4-chloro-5,7-difluoro-2-(5-fluoro-2-(methylsulfonyl)phenyl)-3-methylquinoline. Mass Spectrum (ESI) m/e=386.0 (M+1).

Workup

  1. stirringstirred vigorously for 10 min
  2. filtrationfiltered
  3. dissolutionThe precipitate was dissolved in EtOAc
  4. dry with materialdried over magnesium sulfate

Sources & evidence

ORD record
ord-94239956c8c948e5b3281d507bd4b594
Source dataset
uspto-grants-2015_01
Patent number
US08940724B2

Reaction notes

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