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

HRID 2070025노트

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HRID 2070025 반응식
[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

참가 물질

3

반응물 2

HCID 24813Phosphorus oxychlorideHCID 178490904HCID 178490904, 화합물

생성물 1

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

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온도
70 °C

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-a7e491f730de4668afbcd81c62b6b829
출처 데이터셋
uspto-grants-2012_10
특허 번호
US08299252B2

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