Phosphorus oxybromide → 4-Bromo-2-(2-chloro-6-fluorophenyl)-2H-pyrazolo[4,3-c]pyridine

HRID 626679ノート

反応式

HRID 626679 の反応式
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[N:9]1[CH:18]=[C:12]2[CH:13]=[N+:14]([O-])[CH:15]=[CH:16][C:11]2=[N:10]1.P(Br)(Br)([Br:21])=O>ClCCCl.C(Cl)Cl>[Br:21][C:13]1[C:12]2=[CH:18][N:9]([C:3]3[C:4]([F:8])=[CH:5][CH:6]=[CH:7][C:2]=3[Cl:1])[N:10]=[C:11]2[CH:16]=[CH:15][N:14]=1

参加物

5

反応物 2

HCID 24613Phosphorus oxybromideHCID 696711682-(2-Chloro-6-fluorophenyl)-2H-pyrazolo[4,3-c]pyridine 5-oxide

生成物 1

HCID 866970444-Bromo-2-(2-chloro-6-fluorophenyl)-2H-pyrazolo[4,3-c]pyridine収率 25.2%

試薬・触媒・溶媒 2

HCID 111,2-Dichloroethane溶媒HCID 6344Dichloromethane溶媒

反応条件

温度
0 °C

実験手順

To a suspension of 2-(2-chloro-6-fluorophenyl)-2H-pyrazolo[4,3-c]pyridine 5-oxide (740 mg, 2.8 mmol) in DCE (18 mL) at 0° C. was added phosphorus oxybromide (2.4 g, 8.4 mmol). The reaction mixture was stirred at 0° C. for 15 minutes, warmed to room temperature, and stirred for an additional 4.5 h. The resultant mixture was diluted with DCM, washed with sodium carbonate (sat. aq.) and then with brine. The organic phase was dried over anhydrous magnesium sulphate and concentrated under reduced pressure. The residue was purified by silica gel flash chromatography (0-30% ethyl acetate in cyclohexane) to afford the title compound as a white solid (230 mg, 25% yield). LCMS (Method C): RT=3.44 min, m/z: 327 [M+H+].

後処理

  1. temperaturewarmed to room temperature
  2. stirringstirred for an additional 4.5 h
  3. washwashed with sodium carbonate (sat. aq.)
  4. dry with materialThe organic phase was dried over anhydrous magnesium sulphate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel flash chromatography (0-30% ethyl acetate in cyclohexane)

出典と根拠

ORDレコード
ord-23d6266dc9b548af98fdbb3757fe0551
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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