Phosphorus oxybromide → 4-Bromo-2-(2,6-dichloro-4-vinylphenyl)-7-fluoro-2H-pyrazolo[4,3-c]pyridine

HRID 626804노트

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HRID 626804 반응식
[Cl:1][C:2]1[CH:7]=[C:6]([CH:8]=[CH2:9])[CH:5]=[C:4]([Cl:10])[C:3]=1[N:11]1[CH:21]=[C:14]2[CH:15]=[N+:16]([O-])[CH:17]=[C:18]([F:19])[C:13]2=[N:12]1.P(Br)(Br)([Br:24])=O>C(Cl)Cl>[Br:24][C:15]1[C:14]2=[CH:21][N:11]([C:3]3[C:2]([Cl:1])=[CH:7][C:6]([CH:8]=[CH2:9])=[CH:5][C:4]=3[Cl:10])[N:12]=[C:13]2[C:18]([F:19])=[CH:17][N:16]=1

참가 물질

4

반응물 2

HCID 24613Phosphorus oxybromideHCID 677008712-(2,6-Dichloro-4-vinylphenyl)-7-fluoro-2H-pyrazolo[4,3-c]pyridine 5 oxide

생성물 1

HCID 866970824-Bromo-2-(2,6-dichloro-4-vinylphenyl)-7-fluoro-2H-pyrazolo[4,3-c]pyridine수율 25.3%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

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온도
0 °C

실험 절차

To a suspension of 2-(2,6-dichloro-4-vinylphenyl)-7-fluoro-2H-pyrazolo[4,3-c]pyridine 5 oxide (1.0 g, 3.1 mmol) in DCM (15 mL) under an atmosphere of nitrogen at 0° C., was added phosphorus oxybromide (2.6 g, 9.0 mmol). The reaction mixture was stirred at 0° C. for 1 hour and then allowed to reach room temperature over 30 minutes. The resultant mixture was quenched with saturated aqueous sodium hydrogen carbonate solution and diluted with DCM. The layers were separated and the organic layer was washed with brine, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by silica gel flash chromatography (20% ethyl acetate in cyclohexane) to afford the title compound as a white solid (304 mg, 25% yield). 1H NMR (400 MHz, DMSO-d6): δ 9.41 (d, J=2.5 Hz, 1H), 8.19 (d, J=3.3 Hz, 1H), 7.99 (s, 2H), 6.85 (dd, J=17.6, 11.0 Hz, 1H), 6.25 (d, J=17.6 Hz, 1H), 5.60 (d, J=11.0 Hz, 1H).

후처리

  1. waitto reach room temperature over 30 minutes
  2. customThe resultant mixture was quenched with saturated aqueous sodium hydrogen carbonate solution
  3. additiondiluted with DCM
  4. customThe layers were separated
  5. washthe organic layer was washed with brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was purified by silica gel flash chromatography (20% ethyl acetate in cyclohexane)

출처 및 근거

ORD 기록
ord-fbfdedd603bc4cd3b96cc0125ab29101
출처 데이터셋
uspto-grants-2016_04
특허 번호
US09309240B2

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