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

HRID 626732노트

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HRID 626732 반응식
[Br: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]([Br:1])=[CH:7][N:6]=1

참가 물질

4

반응물 2

HCID 24613Phosphorus oxybromideHCID 696713397-Bromo-2-(2,6-dichlorophenyl)-2H-pyrazolo[4,3-c]pyridine-5-oxide

생성물 1

HCID 866970594,7-Dibromo-2-(2,6-dichlorophenyl)-2H-pyrazolo[4,3-c]pyridine수율 54%

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-bromo-2-(2,6-dichlorophenyl)-2H-pyrazolo[4,3-c]pyridine-5-oxide (1.7 g, 4.7 mmol) in DCE (30 mL) was added phosphorus oxybromide (4.0 g, 14.1 mmol). The reaction mixture was stirred at 0° C. for 15 minutes, warmed to room temperature, and stirred for a further 2.25 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 (0-20% ethyl acetate in cyclohexane) to afford the title compound as a white solid (1.07 g, 54% yield). LCMS (Method D): RT=3.93 min, m/z: 422 [M+H+].

후처리

  1. temperatureTo a cooled
  2. temperaturewarmed to room temperature
  3. stirringstirred for a further 2.25 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 (0-20% ethyl acetate in cyclohexane)

출처 및 근거

ORD 기록
ord-a027bc24e37d4b9bb1ead1208a062348
출처 데이터셋
uspto-grants-2016_04
특허 번호
US09309240B2

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