Bromotrimethylsilane → 2-(4-Bromo-7-fluoropyrazolo[4,3-c]pyridin-2-yl)-3-chlorobenzonitrile

HRID 626755노트

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HRID 626755 반응식
[Cl:1][C:2]1[C:3]([N:10]2[CH:20]=[C:13]3[C:14](Cl)=[N:15][CH:16]=[C:17]([F:18])[C:12]3=[N:11]2)=[C:4]([CH:7]=[CH:8][CH:9]=1)[C:5]#[N:6].[Br:21][Si](C)(C)C>C(#N)CC>[Br:21][C:14]1[C:13]2=[CH:20][N:10]([C:3]3[C:2]([Cl:1])=[CH:9][CH:8]=[CH:7][C:4]=3[C:5]#[N:6])[N:11]=[C:12]2[C:17]([F:18])=[CH:16][N:15]=1

참가 물질

4

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HCID 76113BromotrimethylsilaneHCID 866970653-Chloro-2-(4-chloro-7-fluoropyrazolo[4,3-c]pyridin-2-yl)-benzonitrile

생성물 1

HCID 866970642-(4-Bromo-7-fluoropyrazolo[4,3-c]pyridin-2-yl)-3-chlorobenzonitrile수율 96.1%

시약·촉매·용매 1

HCID 7854Propionitrile용매

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온도
110 °C

실험 절차

3-Chloro-2-(4-chloro-7-fluoropyrazolo[4,3-c]pyridin-2-yl)-benzonitrile (890 mg, 2.9 mmol) was suspended in propionitrile (30 mL), under an atmosphere of nitrogen and bromotrimethylsilane (2.0 mL, 15 mmol) was added. The reaction mixture was heated at 110° C. for 3.5 hours. 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 organic layer was washed with brine, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The residue was triturated with diethyl ether to afford the title compound as a yellow solid (980 mg, 96% yield). 1H NMR (400 MHz, DMSO-d6): δ 9.54 (d, J=2.5 Hz, 1H), 8.25-8.21 (m, 3H), 7.94 (t, J=8.1 Hz, 1H).

후처리

  1. custompartitioned between ethyl acetate and 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
  7. customThe residue was triturated with diethyl ether

출처 및 근거

ORD 기록
ord-cc36a3099d1544d4b17b8bdb1968e209
출처 데이터셋
uspto-grants-2016_04
특허 번호
US09309240B2

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