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

HRID 626796
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HRID 626796 반응식
Cl[C:2]1[C:7]2=[CH:8][N:9]([C:11]3[C:16]([F:17])=[CH:15][CH:14]=[CH:13][C:12]=3[Cl:18])[N:10]=[C:6]2[C:5]([F:19])=[CH:4][N:3]=1.[Br:20][Si](C)(C)C>C(#N)CC.C(OCC)(=O)C>[Br:20][C:2]1[C:7]2=[CH:8][N:9]([C:11]3[C:16]([F:17])=[CH:15][CH:14]=[CH:13][C:12]=3[Cl:18])[N:10]=[C:6]2[C:5]([F:19])=[CH:4][N:3]=1
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5

반응물 2

HCID 76113BromotrimethylsilaneHCID 866970804-Chloro-2-(2-chloro-6-fluorophenyl)-7-fluoro-2H-pyrazolo[4,3-c]pyridine

생성물 1

HCID 866970814-Bromo-2-(2-chloro-6-fluorophenyl)-7-fluoro-2H-pyrazolo[4,3-c]pyridine수율 100.6%

시약·촉매·용매 2

HCID 7854Propionitrile용매HCID 8857Ethyl Acetate용매

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온도
100 °C

실험 절차

4-Chloro-2-(2-chloro-6-fluorophenyl)-7-fluoro-2H-pyrazolo[4,3-c]pyridine (3.05 g, 10.1 mmol) was suspended in propionitrile (60 mL) under an atmosphere of nitrogen and bromotrimethylsilane (4.0 mL, 30.0 mmol) was added. The reaction mixture was heated at 100° C. overnight. The resultant mixture was cooled to room temperature, diluted with ethyl acetate and washed with saturated aqueous sodium bicarbonate solution. The layers were separated and the organic layer was washed with brine, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to afford the title compound as a beige solid (3.5 g, 100% yield). This was used directly in the next step without further purification. 1H NMR (400 MHz, DMSO-d6): δ 9.46 (d, J=2.5 Hz, 1H), 8.21 (d, J=3.4 Hz, 1H), 7.85-7.77 (m, 1H), 7.74-7.64 (m, 2H).

후처리

  1. washwashed with saturated aqueous sodium bicarbonate solution
  2. customThe layers were separated
  3. washthe organic layer was washed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-0d70136bd43446aa82a3f3a6377fb568
출처 데이터셋
uspto-grants-2016_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09309240B2

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