Phosphorus oxybromide → 4bromo-7-chloro-2-(2,6-dichlorophenyl)-2H-pyrazolo[4,3-c]pyridine

HRID 626712노트

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HRID 626712 반응식
[Cl:1][C:2]1[C:3]2[C:4](=[CH:9][N:10]([C:12]3[C:17]([Cl:18])=[CH:16][CH:15]=[CH:14][C:13]=3[Cl:19])[N:11]=2)[CH:5]=[N+:6]([O-])[CH:7]=1.P(Br)(Br)([Br:22])=O>ClCCCl>[Br:22][C:5]1[C:4]2=[CH:9][N:10]([C:12]3[C:17]([Cl:18])=[CH:16][CH:15]=[CH:14][C:13]=3[Cl:19])[N:11]=[C:3]2[C:2]([Cl:1])=[CH:7][N:6]=1

참가 물질

4

반응물 2

HCID 24613Phosphorus oxybromideHCID 696716927-Chloro-2-(2,6-dichlorophenyl)-2H-pyrazolo[4,3-c]pyridine-5-oxide

생성물 1

HCID 866970524bromo-7-chloro-2-(2,6-dichlorophenyl)-2H-pyrazolo[4,3-c]pyridine수율 28.1%

시약·촉매·용매 1

HCID 111,2-Dichloroethane용매

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온도
0 °C

실험 절차

To a cooled (0° C.) suspension of 7-chloro-2-(2,6-dichlorophenyl)-2H-pyrazolo[4,3-c]pyridine-5-oxide (2.5 g, 8.0 mmol) in DCE (50 mL) was added phosphorus oxybromide (6.8 g, 24.0 mmol). The reaction mixture was stirred at 0° C. for 30 minutes, warmed to room temperature, and stirred for a further 18 hours. The reaction mixture was partitioned between DCM and sodium carbonate (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 flash chromatography (0-50% ethyl acetate in cyclohexane) to afford the title compound as a white solid (850 mg, 28% yield). LCMS (Method D): RT=3.92 min, m/z: 377 [M+H+].

후처리

  1. temperatureTo a cooled
  2. temperaturewarmed to room temperature
  3. stirringstirred for a further 18 hours
  4. customThe reaction mixture was partitioned between DCM and sodium carbonate (sat. aq.)
  5. washThe organic layer was washed with brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by silica gel flash chromatography (0-50% ethyl acetate in cyclohexane)

출처 및 근거

ORD 기록
ord-8dcf5c73ec7d463f8f72b83bc7f58d31
출처 데이터셋
uspto-grants-2016_04
특허 번호
US09309240B2

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