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

HRID 1618542노트

반응식

HRID 1618542 반응식
[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]

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 30318Osmium Tetroxide촉매HCID 180Acetone용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-8acf550d082046809d97fac6cc3ae1db
출처 데이터셋
uspto-grants-2014_07
특허 번호
US08765940B2

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