Tetrahydrofuran → HCID 59631240, compound

HRID 1431642Notes

Reaction equation

HRID 1431642 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

The 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 ppt. was dissolved in EtOAc (50 mL) and dried over magnesium sulfate. The filtrate was cond to give crude 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. dissolutionwas dissolved in EtOAc (50 mL)
  5. dry with materialdried over magnesium sulfate

Sources & evidence

ORD record
ord-6987687eb2ee4281b85254754409fae8
Source dataset
uspto-grants-2015_01
Patent number
US08940724B2

Reaction notes

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