Phosphorus oxybromide → 4-Bromo-2-(2-chloro-6-fluorophenyl)-2H-pyrazolo[4,3-c]pyridine

HRID 626679노트

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HRID 626679 반응식
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[N:9]1[CH:18]=[C:12]2[CH:13]=[N+:14]([O-])[CH:15]=[CH:16][C:11]2=[N:10]1.P(Br)(Br)([Br:21])=O>ClCCCl.C(Cl)Cl>[Br:21][C:13]1[C:12]2=[CH:18][N:9]([C:3]3[C:4]([F:8])=[CH:5][CH:6]=[CH:7][C:2]=3[Cl:1])[N:10]=[C:11]2[CH:16]=[CH:15][N:14]=1

참가 물질

5

반응물 2

HCID 24613Phosphorus oxybromideHCID 696711682-(2-Chloro-6-fluorophenyl)-2H-pyrazolo[4,3-c]pyridine 5-oxide

생성물 1

HCID 866970444-Bromo-2-(2-chloro-6-fluorophenyl)-2H-pyrazolo[4,3-c]pyridine수율 25.2%

시약·촉매·용매 2

HCID 111,2-Dichloroethane용매HCID 6344Dichloromethane용매

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온도
0 °C

실험 절차

To a suspension of 2-(2-chloro-6-fluorophenyl)-2H-pyrazolo[4,3-c]pyridine 5-oxide (740 mg, 2.8 mmol) in DCE (18 mL) at 0° C. was added phosphorus oxybromide (2.4 g, 8.4 mmol). The reaction mixture was stirred at 0° C. for 15 minutes, warmed to room temperature, and stirred for an additional 4.5 h. The resultant mixture was diluted with DCM, washed with sodium carbonate (sat. aq.) and then with brine. The organic phase was dried over anhydrous magnesium sulphate and concentrated under reduced pressure. The residue was purified by silica gel flash chromatography (0-30% ethyl acetate in cyclohexane) to afford the title compound as a white solid (230 mg, 25% yield). LCMS (Method C): RT=3.44 min, m/z: 327 [M+H+].

후처리

  1. temperaturewarmed to room temperature
  2. stirringstirred for an additional 4.5 h
  3. washwashed with sodium carbonate (sat. aq.)
  4. dry with materialThe organic phase was dried over anhydrous magnesium sulphate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel flash chromatography (0-30% ethyl acetate in cyclohexane)

출처 및 근거

ORD 기록
ord-23d6266dc9b548af98fdbb3757fe0551
출처 데이터셋
uspto-grants-2016_04
특허 번호
US09309240B2

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