Hydrogen Peroxide → 7-Bromo-2-(2,6-dichlorophenyl)-2H-pyrazolo[4,3-c]pyridine-5-oxide

HRID 626731ノート

反応式

HRID 626731 の反応式
[Br:1][C:2]1[C:3]2[C:4](=[CH:8][N:9]([C:11]3[C:16]([Cl:17])=[CH:15][CH:14]=[CH:13][C:12]=3[Cl:18])[N:10]=2)[CH:5]=[N:6][CH:7]=1.[OH:19]O>C(Cl)Cl.C[Re](=O)(=O)=O>[Br:1][C:2]1[C:3]2[C:4](=[CH:8][N:9]([C:11]3[C:16]([Cl:17])=[CH:15][CH:14]=[CH:13][C:12]=3[Cl:18])[N:10]=2)[CH:5]=[N+:6]([O-:19])[CH:7]=1

参加物

5

反応物 2

HCID 784Hydrogen PeroxideHCID 696713917-bromo-2-(2,6-dichlorophenyl)-2H-pyrazolo[4,3-c]pyridine

生成物 1

HCID 696713397-Bromo-2-(2,6-dichlorophenyl)-2H-pyrazolo[4,3-c]pyridine-5-oxide収率 47.4%

試薬・触媒・溶媒 2

HCID 178477782HCID 178477782、化合物触媒HCID 6344Dichloromethane溶媒

実験手順

To a solution of 7-bromo-2-(2,6-dichlorophenyl)-2H-pyrazolo[4,3-c]pyridine (3.43 g, 10 mmol) and methyltrioxorhenium (249 mg, 1.0 mmol) in DCM (35 mL) was added hydrogen peroxide (30% aq., 1.95 mL, 20 mmol) and the resulting mixture stirred at room temperature for 18 hours. The reaction mixture was partitioned between DCM and sodium bicarbonate (sat. aq.). The organic layer was washed with brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel chromatography (0-5% methanol in DCM) to afford the title compound as a beige solid (1.7 g, 47% yield). LCMS (Method D): RT=2.46 min, m/z: 360 [M+H+].

後処理

  1. customThe reaction mixture was partitioned between DCM and sodium bicarbonate (sat. aq.)
  2. washThe organic layer was washed with brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel chromatography (0-5% methanol in DCM)

出典と根拠

ORDレコード
ord-f10ca1ea828f44b5ba6bed3ea837fada
出典データセット
uspto-grants-2016_04
特許番号
US09309240B2

反応ノート

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