HCID 86606800, 화합물 → 6-(4-Fluorophenyl)-2-methyl-4-(3-pyridyl)-5-(4-pyridyl)pyrazolo[3,4-b]pyridine

HRID 42611노트

반응식

HRID 42611 반응식
Cl[C:2]1[N:7]=[CH:6][C:5]([C:8]2[C:9]3[C:10](=[N:27][N:28]([CH3:30])[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:19]=[CH:18][N:17]=[CH:16][CH:15]=2)=[CH:4][CH:3]=1>CC(O)=O.[Zn]>[F:26][C:23]1[CH:22]=[CH:21][C:20]([C:12]2[C:13]([C:14]3[CH:15]=[CH:16][N:17]=[CH:18][CH:19]=3)=[C:8]([C:5]3[CH:6]=[N:7][CH:2]=[CH:3][CH:4]=3)[C:9]3[C:10](=[N:27][N:28]([CH3:30])[CH:29]=3)[N:11]=2)=[CH:25][CH:24]=1

참가 물질

4

반응물 1

HCID 86606800HCID 86606800, 화합물

생성물 1

HCID 104524286-(4-Fluorophenyl)-2-methyl-4-(3-pyridyl)-5-(4-pyridyl)pyrazolo[3,4-b]pyridine수율 4%

시약·촉매·용매 2

HCID 23994Zinc촉매HCID 176Acetic Acid용매

실험 절차

To a solution of 4-(6-chloropyridin-3-yl)-6-(4-fluorophenyl)-2-methyl-5-(4-pyridyl)pyrazolo[3,4-b]pyridine (74 mg, 0.2 mmol, obtained in example 193) in AcOH (1 mL), Zn (72 mg, 1.1 mmol) was added under argon atmosphere and the mixture was heated to reflux overnight. It was allowed to cool and concentrated. The residue was treated with saturated NaHCO3 and it was extracted with CHCl3. The organic phase was dried over Na2SO4 and concentrated to dryness. The crude product obtained was purified by chromatography on silica gel using hexane-EtOAc-MeOH mixtures of increasing polarity, to afford 2.4 mg of the title compound (yield: 4%)

후처리

  1. temperaturethe mixture was heated
  2. temperatureto reflux overnight
  3. temperatureto cool
  4. concentrationconcentrated
  5. additionThe residue was treated with saturated NaHCO3 and it
  6. extractionwas extracted with CHCl3
  7. dry with materialThe organic phase was dried over Na2SO4
  8. concentrationconcentrated to dryness
  9. customThe crude product obtained
  10. customwas purified by chromatography on silica gel
  11. temperatureof increasing polarity

출처 및 근거

ORD 기록
ord-85650d0182d54290931a6323088b9d36
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08536194B2

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