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

HRID 1618542ノート

反応式

HRID 1618542 の反応式
[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]

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 30318Osmium Tetroxide触媒HCID 180Acetone溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-8acf550d082046809d97fac6cc3ae1db
出典データセット
uspto-grants-2014_07
特許番号
US08765940B2

反応ノート

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