Water → 4-Chloro-7-fluoro-3-methyl-2-(2-(methylsulfonyl)phenyl)quinoline

HRID 1618542Notes

Reaction equation

HRID 1618542 reaction equation
[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([F:12])=[CH:9][CH:10]=2)[N:5]=[C:4]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[S:19][CH3:20])[C:3]=1[CH3:21].[OH2:22].C[N+]1([O-])CC[O:27]CC1>CC(C)=O.[Os](=O)(=O)(=O)=O>[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([F:12])=[CH:9][CH:10]=2)[N:5]=[C:4]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[S:19]([CH3:20])(=[O:27])=[O:22])[C:3]=1[CH3:21]

Participants

6

Reactant 3

HCID 962WaterHCID 82029Methyl morpholine oxideHCID 672849044-Chloro-7-fluoro-3-methyl-2-(2-(methylthio)phenyl)quinoline

Product 1

HCID 672846274-Chloro-7-fluoro-3-methyl-2-(2-(methylsulfonyl)phenyl)quinoline

Reagents, catalysts & solvents 2

HCID 30318Osmium TetroxideCatalystHCID 180AcetoneSolvent

Procedure

To a solution of 4-chloro-7-fluoro-3-methyl-2-(2-(methylthio)phenyl)quinoline (95 mg, 0.30 mmol) (described herein) in acetone (3.5 mL) and water (0.88 mL) was sequentially added NMO (105 mg, 0.90 mmol) and osmium tetroxide (4.7 μL, 0.015 mmol). The reaction mixture was stirred at rt for 35 h, then quenched with 15 mL 10% aqueous sodium thiosulfate solution, concentrated to remove the acetone, and partitioned between EtOAc and 10% aqueous sodium thiosulfate solution. The organic layer was washed with brine, dried (MgSO4), and concentrated, affording 4-chloro-7-fluoro-3-methyl-2-(2-(methylsulfonyl)-phenyl)quinoline. Mass Spectrum (ESI) m/e=350 (M+1).

Workup

  1. customquenched with 15 mL 10% aqueous sodium thiosulfate solution
  2. concentrationconcentrated
  3. customto remove the acetone
  4. custompartitioned between EtOAc and 10% aqueous sodium thiosulfate solution
  5. washThe organic layer was washed with brine
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-8acf550d082046809d97fac6cc3ae1db
Source dataset
uspto-grants-2014_07
Patent number
US08765940B2

Reaction notes

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