Formaldehyde → [4,6-Bis(4-fluorophenyl)-5-(4-pyridyl)pyrazolo[3,4-b]pyridin-2-yl]methanol

HRID 42590노트

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HRID 42590 반응식
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:13]([C:14]3[CH:19]=[CH:18][N:17]=[CH:16][CH:15]=3)=[C:12]([C:20]3[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=3)[N:11]=[C:10]3[NH:27][N:28]=[CH:29][C:9]=23)=[CH:4][CH:3]=1.[CH2:30]=[O:31]>>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9]3[C:10](=[N:27][N:28]([CH2:30][OH:31])[CH:29]=3)[N:11]=[C:12]([C:20]3[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=3)[C:13]=2[C:14]2[CH:15]=[CH:16][N:17]=[CH:18][CH:19]=2)=[CH:4][CH:3]=1

참가 물질

3

반응물 2

HCID 712FormaldehydeHCID 119613744,6-Bis(4-fluorophenyl)-5-(4-pyridyl)-1H-pyrazolo[3,4-b]pyridine

생성물 1

HCID 68443653[4,6-Bis(4-fluorophenyl)-5-(4-pyridyl)pyrazolo[3,4-b]pyridin-2-yl]methanol수율 65%

반응 조건

온도
130 °C

실험 절차

A suspension of 4,6-bis(4-fluorophenyl)-5-(4-pyridyl)-1H-pyrazolo[3,4-b]pyridine (0.20 g, 0.5 mmol, obtained in example 1) in 30-40% aqueous formaldehyde (0.9 mL) was stirred at 130° C. under argon atmosphere for 4 h. The solvent was concentrated and the residue was dissolved in a mixture of CHCl3 and water and the phases were separated. The organic phase was dried over Na2SO4 and concentrated to dryness. The crude product obtained was purified on chromatography on silica gel using hexane-EtOAc mixtures of increasing polarity as eluent, to afford 140 mg of the title compound in solid form (yield: 65%).

후처리

  1. concentrationThe solvent was concentrated
  2. dissolutionthe residue was dissolved in a mixture of CHCl3 and water
  3. customthe phases were separated
  4. dry with materialThe organic phase was dried over Na2SO4
  5. concentrationconcentrated to dryness
  6. customThe crude product obtained
  7. customwas purified on chromatography on silica gel
  8. temperatureof increasing polarity as eluent

출처 및 근거

ORD 기록
ord-c189d64351e4427481208ea5fd6319ed
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08536194B2

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