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

HRID 626767ノート

反応式

HRID 626767 の反応式
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

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 7854Propionitrile溶媒

反応条件

温度
105 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-b06392de6d824a1abbd8f5ddd3ad4af1
出典データセット
uspto-grants-2016_04
特許番号
US09309240B2

反応ノート

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