Bromotrimethylsilane → 4-Bromo-2-(2,6-dichloro-4-nitrophenyl)-7-fluoro-2H-pyrazolo[4,3-c]pyridine

HRID 626767노트

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HRID 626767 반응식
Cl[C:2]1[C:7]2=[CH:8][N:9]([C:11]3[C:16]([Cl:17])=[CH:15][C:14]([N+:18]([O-:20])=[O:19])=[CH:13][C:12]=3[Cl:21])[N:10]=[C:6]2[C:5]([F:22])=[CH:4][N:3]=1.[Br:23][Si](C)(C)C>C(#N)CC>[Br:23][C:2]1[C:7]2=[CH:8][N:9]([C:11]3[C:16]([Cl:17])=[CH:15][C:14]([N+:18]([O-:20])=[O:19])=[CH:13][C:12]=3[Cl:21])[N:10]=[C:6]2[C:5]([F:22])=[CH:4][N:3]=1

참가 물질

4

반응물 2

HCID 76113BromotrimethylsilaneHCID 866970684-Chloro-2-(2,6-dichloro-4-nitrophenyl)-7-fluoro-2H-pyrazolo[4,3-c]pyridine

생성물 1

HCID 866970694-Bromo-2-(2,6-dichloro-4-nitrophenyl)-7-fluoro-2H-pyrazolo[4,3-c]pyridine수율 102.9%

시약·촉매·용매 1

HCID 7854Propionitrile용매

반응 조건

온도
105 °C

실험 절차

4-Chloro-2-(2,6-dichloro-4-nitrophenyl)-7-fluoro-2H-pyrazolo[4,3-c]pyridine (1.78 g, 4.93 mmol) was suspended in propionitrile (30 mL), under an atmosphere of nitrogen and bromo trimethylsilane (5.1 mL, 38.3 mmol) was added. The reaction mixture was heated at 105° C. overnight. The resultant mixture was cooled to room temperature and partitioned between ethyl acetate and saturated aqueous sodium bicarbonate solution. The layers were separated and the aqueous layer was further extracted with ethyl acetate (×2). The combined organic layers were dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The residue was triturated with pentane and the solid obtained was dried under reduced pressure to afford the title compound as a pale yellow solid (2.06 g, quantitative yield). 1H NMR (300 MHz, CDCl3): δ 8.44 (s, 2H), 8.33 (d, J=2.2 Hz, 1H), 8.05 (d, J=3.0 Hz, 1H).

후처리

  1. custompartitioned between ethyl acetate and saturated aqueous sodium bicarbonate solution
  2. customThe layers were separated
  3. extractionthe aqueous layer was further extracted with ethyl acetate (×2)
  4. dry with materialThe combined organic layers were dried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was triturated with pentane
  8. customthe solid obtained
  9. customwas dried under reduced pressure

출처 및 근거

ORD 기록
ord-b06392de6d824a1abbd8f5ddd3ad4af1
출처 데이터셋
uspto-grants-2016_04
특허 번호
US09309240B2

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