Phosphorus oxybromide → 4,7-Dibromo-2-(2,6-dichlorophenyl)-2H-pyrazolo[4,3-c]pyridine

HRID 626732ノート

反応式

HRID 626732 の反応式
[Br:1][C:2]1[C:3]2[C:4](=[CH:9][N:10]([C:12]3[C:17]([Cl:18])=[CH:16][CH:15]=[CH:14][C:13]=3[Cl:19])[N:11]=2)[CH:5]=[N+:6]([O-])[CH:7]=1.P(Br)(Br)([Br:22])=O>ClCCCl>[Br:22][C:5]1[C:4]2=[CH:9][N:10]([C:12]3[C:17]([Cl:18])=[CH:16][CH:15]=[CH:14][C:13]=3[Cl:19])[N:11]=[C:3]2[C:2]([Br:1])=[CH:7][N:6]=1

参加物

4

反応物 2

HCID 24613Phosphorus oxybromideHCID 696713397-Bromo-2-(2,6-dichlorophenyl)-2H-pyrazolo[4,3-c]pyridine-5-oxide

生成物 1

HCID 866970594,7-Dibromo-2-(2,6-dichlorophenyl)-2H-pyrazolo[4,3-c]pyridine収率 54%

試薬・触媒・溶媒 1

HCID 111,2-Dichloroethane溶媒

反応条件

温度
0 °C

実験手順

To a cooled (0° C.) suspension of 7-bromo-2-(2,6-dichlorophenyl)-2H-pyrazolo[4,3-c]pyridine-5-oxide (1.7 g, 4.7 mmol) in DCE (30 mL) was added phosphorus oxybromide (4.0 g, 14.1 mmol). The reaction mixture was stirred at 0° C. for 15 minutes, warmed to room temperature, and stirred for a further 2.25 hours. The reaction mixture was partitioned between DCM and sodium carbonate (sat. aq.). The organic layer was washed with brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel flash chromatography (0-20% ethyl acetate in cyclohexane) to afford the title compound as a white solid (1.07 g, 54% yield). LCMS (Method D): RT=3.93 min, m/z: 422 [M+H+].

後処理

  1. temperatureTo a cooled
  2. temperaturewarmed to room temperature
  3. stirringstirred for a further 2.25 hours
  4. customThe reaction mixture was partitioned between DCM and sodium carbonate (sat. aq.)
  5. washThe organic layer was washed with brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by silica gel flash chromatography (0-20% ethyl acetate in cyclohexane)

出典と根拠

ORDレコード
ord-a027bc24e37d4b9bb1ead1208a062348
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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