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

HRID 42611ノート

反応式

HRID 42611 の反応式
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

参加物

4

反応物 1

HCID 86606800HCID 86606800、化合物

生成物 1

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

試薬・触媒・溶媒 2

HCID 23994Zinc触媒HCID 176Acetic Acid溶媒

実験手順

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%)

後処理

  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

出典と根拠

ORDレコード
ord-85650d0182d54290931a6323088b9d36
出典データセット
uspto-grants-2013_09
特許番号
US08536194B2

反応ノート

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