Phosphorus oxychloride → 4-chloro-1-(4-methoxybenzyl)-1H-pyrazolo[3,4-b]pyridine

HRID 2070025ノート

反応式

HRID 2070025 の反応式
[CH3:1][O:2][C:3]1[CH:19]=[CH:18][C:6]([CH2:7][N:8]2[C:12]3[N:13]=[CH:14][CH:15]=[C:16](O)[C:11]=3[CH:10]=[N:9]2)=[CH:5][CH:4]=1.P(Cl)(Cl)([Cl:22])=O>>[Cl:22][C:16]1[CH:15]=[CH:14][N:13]=[C:12]2[N:8]([CH2:7][C:6]3[CH:18]=[CH:19][C:3]([O:2][CH3:1])=[CH:4][CH:5]=3)[N:9]=[CH:10][C:11]=12

参加物

3

反応物 2

HCID 24813Phosphorus oxychlorideHCID 178490904HCID 178490904、化合物

生成物 1

HCID 593985764-chloro-1-(4-methoxybenzyl)-1H-pyrazolo[3,4-b]pyridine収率 70%

反応条件

温度
70 °C

実験手順

1-(4-Methoxybenzyl)-1H-pyrazolo[3,4-b]pyridin-4-ol (759 mg) was dissolved in phosphorus oxychloride (6 mL). The resulting mixture was stirred at 70° C. for 1 hour. The reaction solution was concentrated under reduced pressure. The residue was diluted with ethyl acetate and carefully washed with a sodium bicarbonate solution. The organic layer was dried (using sodium sulfate), and the drying agent was removed by filtration. The filtrate was concentrated under reduced pressure. The obtained residue was purified by silica-gel column chromatography (hexane/ethyl acetate=5/0 to 3/1) to give 4-chloro-1-(4-methoxybenzyl)-1H-pyrazolo[3,4-b]pyridine (568 mg, yield: 70%) as a colorless solid.

後処理

  1. concentrationThe reaction solution was concentrated under reduced pressure
  2. additionThe residue was diluted with ethyl acetate
  3. washcarefully washed with a sodium bicarbonate solution
  4. dry with materialThe organic layer was dried (using sodium sulfate)
  5. customthe drying agent was removed by filtration
  6. concentrationThe filtrate was concentrated under reduced pressure
  7. customThe obtained residue was purified by silica-gel column chromatography (hexane/ethyl acetate=5/0 to 3/1)

出典と根拠

ORDレコード
ord-a7e491f730de4668afbcd81c62b6b829
出典データセット
uspto-grants-2012_10
特許番号
US08299252B2

反応ノート

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