m-Chloroperbenzoic acid → 2-(2,6-Dichloro-4-fluorophenyl)-7-fluoro-2H-pyrazolo[4,3-c]pyridine-5-oxide

HRID 626743ノート

反応式

HRID 626743 の反応式
[Cl:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[C:4]([Cl:9])[C:3]=1[N:10]1[CH:19]=[C:13]2[CH:14]=[N:15][CH:16]=[C:17]([F:18])[C:12]2=[N:11]1.C1C=C(Cl)C=C(C(OO)=[O:28])C=1>C(Cl)Cl>[Cl:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[C:4]([Cl:9])[C:3]=1[N:10]1[CH:19]=[C:13]2[CH:14]=[N+:15]([O-:28])[CH:16]=[C:17]([F:18])[C:12]2=[N:11]1

参加物

4

反応物 2

HCID 70297m-Chloroperbenzoic acidHCID 696717192-(2,6-dichloro-4-fluorophenyl)-7-fluoro-2H-pyrazolo[4,3-c]pyridine

生成物 1

HCID 696711692-(2,6-Dichloro-4-fluorophenyl)-7-fluoro-2H-pyrazolo[4,3-c]pyridine-5-oxide収率 84.2%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
0 °C

実験手順

To a cooled (0° C.) solution of 2-(2,6-dichloro-4-fluorophenyl)-7-fluoro-2H-pyrazolo[4,3-c]pyridine (3.37 g, 11.2 mmol) in DCM (50 mL) under nitrogen, was added mCPBA (2.9 g, 16.8 mmol). The reaction mixture was stirred at 0° C. for 2 hours, warmed to room temperature, and stirred for a further 5 hours. The reaction was washed with sodium thiosulfate (sat. aq.), sodium hydrogen carbonate (sat. aq.), and brine. The organic layer was then dried over anhydrous sodium sulphate and concentrated under reduced pressure. The residue was purified by trituration with diethyl ether to afford the title compound as an off-white solid (2.98 g, 84% yield). LCMS (Method D): RT=2.48 min, m/z: 316 [M+H+].

後処理

  1. temperaturewarmed to room temperature
  2. stirringstirred for a further 5 hours
  3. washThe reaction was washed with sodium thiosulfate (sat. aq.), sodium hydrogen carbonate (sat. aq.), and brine
  4. dry with materialThe organic layer was then dried over anhydrous sodium sulphate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by trituration with diethyl ether

出典と根拠

ORDレコード
ord-a9aaa562948041c4b8e55cfd55092194
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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