Phosphorus oxychloride → ethyl 6-chloro-1H-pyrazolo(3,4-b)pyridine-4-carboxylate

HRID 82021노트

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HRID 82021 반응식
[CH2:1]([O:3][C:4]([C:6]1[C:7]2[CH:15]=[N:14][NH:13][C:8]=2[N:9]=[C:10](O)[CH:11]=1)=[O:5])[CH3:2].P(Cl)(Cl)([Cl:18])=O>>[CH2:1]([O:3][C:4]([C:6]1[C:7]2[CH:15]=[N:14][NH:13][C:8]=2[N:9]=[C:10]([Cl:18])[CH:11]=1)=[O:5])[CH3:2]

참가 물질

3

반응물 2

HCID 24813Phosphorus oxychlorideHCID 178469358ethyl 6-oxo-1,2-dihydropyrazolo[3,4-b]pyridine-4-carboxylate

생성물 1

HCID 86678157ethyl 6-chloro-1H-pyrazolo(3,4-b)pyridine-4-carboxylate수율 21%

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온도
110 °C

실험 절차

A mixture of 6-hydroxy-1H-pyrazolo[3,4-b]pyridine-4-carboxylic acid ethyl ester (116.4 g, 0.562 mol) and phosphorus oxychloride (500 mL) was heated at 110° C. for 6 hours then cooled to room temperature before being evaporated under reduced pressure. The residue was taken up in EtOAc and the precipitate filtered. The filtrate was neutralized using triethylamine (500 mL) and the resulting salt filtered. The filtrate was concentrated under vacuum and the residue subjected to silica gel column chromatography using a 9/1 mixture of toluene/EtOAc to afford the title compound as a yellow solid (26.3 g, 21%).

후처리

  1. temperaturethen cooled to room temperature
  2. custombefore being evaporated under reduced pressure
  3. filtrationthe precipitate filtered
  4. filtrationthe resulting salt filtered
  5. concentrationThe filtrate was concentrated under vacuum
  6. additiona 9/1 mixture of toluene/EtOAc

출처 및 근거

ORD 기록
ord-2e142686eb7b43f5b7fabf52ef3aa8ed
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08846712B2

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