Tetrahydrofuran → HCID 59631248, compound

HRID 1431629Notes

Reaction equation

HRID 1431629 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]([O:20][C:21]([F:24])([F:23])[F:22])[CH:17]=[CH:16][C:15]=2SC)[C:3]=1[CH3:27].O[O:29][S:30]([O-:32])=O.[K+].[CH2:34]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]([O:20][C:21]([F:22])([F:23])[F:24])[CH:17]=[CH:16][C:15]=2[S:30]([CH3:34])(=[O:32])=[O:29])[C:3]=1[CH3:27]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 23707502Potassium hydroxy sulfiteHCID 59631118HCID 59631118, compound

Product 1

HCID 59631248HCID 59631248, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

The 4-chloro-5,7-difluoro-3-methyl-2-(2-(methylthio)-5-(trifluoromethoxy)-phenyl)quinoline (560 mg, 1.30 mmol) was dissolved in a mixture of THF (10.0 mL) and water (3.3 mL). To the solution was added Oxone™ (2.1 g, 3.3 mmol) and the resulting slurry was stirred vigorously 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-3-methyl-2-(2-(methylsulfonyl)-5-(trifluoromethoxy)phenyl)quinoline. Mass Spectrum (ESI) m/e=452.0 (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-04cb20597a1247889121db574abbdda0
Source dataset
uspto-grants-2015_01
Patent number
US08940724B2

Reaction notes

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