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

HRID 626743노트

반응식

HRID 626743 반응식
[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

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

반응 조건

온도
0 °C

실험 절차

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+].

후처리

  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

출처 및 근거

ORD 기록
ord-a9aaa562948041c4b8e55cfd55092194
출처 데이터셋
uspto-grants-2016_04
특허 번호
US09309240B2

반응 노트

불러오는 중…