Tetrahydrofuran → HCID 59631240, compound

HRID 1618716Notes

Reaction equation

HRID 1618716 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]([CH3:20])[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]([CH3:20])[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 59631382HCID 59631382, compound

Product 1

HCID 59631240HCID 59631240, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

4-Chloro-5,7-difluoro-3-methyl-2-(5-methyl-2-(methylthio)phenyl)quinoline (160 mg, 0.46 mmol) was slurried in a mixture of THF (3.4 mL) and water (1.1 mL). Oxone™ (700 mg, 1.1 mmol) was added and the mixture was stirred vigorously overnight. The reaction mixture was then poured into water (25 mL) and stirred for 10 min. The mixture was then filtered and washed with water. The precipitate was dissolved in EtOAc (50 mL) and dried over MgSO4. The filtrate was concentrated to give 4-chloro-5,7-difluoro-3-methyl-2-(5-methyl-2-(methylsulfonyl)phenyl)-quinoline. Mass Spectrum (ESI) m/e=382.0 (M+1).

Workup

  1. stirringstirred for 10 min
  2. filtrationThe mixture was then filtered
  3. washwashed with water
  4. dissolutionThe precipitate was dissolved in EtOAc (50 mL)
  5. dry with materialdried over MgSO4
  6. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-218239cd70e54955a6ce15389a4b820e
Source dataset
uspto-grants-2014_07
Patent number
US08765940B2

Reaction notes

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