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

HRID 42611Notes

Reaction equation

HRID 42611 reaction equation
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

Participants

4

Reactant 1

HCID 86606800HCID 86606800, compound

Product 1

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

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 176Acetic AcidSolvent

Procedure

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%)

Workup

  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

Sources & evidence

ORD record
ord-85650d0182d54290931a6323088b9d36
Source dataset
uspto-grants-2013_09
Patent number
US08536194B2

Reaction notes

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