Potassium Hydroxide → HCID 11581244, compound

HRID 2373224Notes

Reaction equation

HRID 2373224 reaction equation
[CH2:1]([N:3]1[C:7]2=[N:8][C:9]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)=[C:10]([C:19]([O:21]CC)=[O:20])[C:11]([C:12]3[CH:13]=[N:14][CH:15]=[C:16]([CH3:18])[CH:17]=3)=[C:6]2[CH:5]=[N:4]1)[CH3:2].[OH-].[K+]>CCO.O>[CH2:1]([N:3]1[C:7]2=[N:8][C:9]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)=[C:10]([C:19]([OH:21])=[O:20])[C:11]([C:12]3[CH:13]=[N:14][CH:15]=[C:16]([CH3:18])[CH:17]=3)=[C:6]2[CH:5]=[N:4]1)[CH3:2]

Participants

5

Reactant 2

HCID 14797Potassium Hydroxide2×HCID 69184934HCID 69184934, compound

Product 1

HCID 11581244HCID 11581244, compoundYield 70.5%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent2×

Procedure

To a stirred solution of ethyl 1-ethyl-4-(5-methyl-3-pyridyl)-6-phenyl-1H-pyrazolo[3,4-b]pyridine-5-carboxylate (257 mg) in a mixture of EtOH (2.5 ml) and water (2 ml) was added potassium hydroxide (1.32 g) and the mixture was refluxed for 12 hours. Another potassium hydroxide (439 mg) was added and the mixture was refluxed for 4.5 hours. After cooling, the reaction mixture was diluted with water and extracted with CHCl3. The aqueous layer was acidified to pH3-4 by adding HCl and extracted with CHCl3. The organic layer was washed with water, dried over anhydrous MgSO4 and concentrated in vacuo. The residue was crystallized from EtOAc and n-hexane to give 1-ethyl-4-(5-methyl-3-pyridyl)-6-phenyl-1H-pyrazolo [3,4-b]pyridine-5-carboxylic acid (168 mg) as a light yellow crystal.

Workup

  1. temperaturethe mixture was refluxed for 12 hours
  2. temperaturethe mixture was refluxed for 4.5 hours
  3. temperatureAfter cooling
  4. extractionextracted with CHCl3
  5. additionby adding HCl
  6. extractionextracted with CHCl3
  7. washThe organic layer was washed with water
  8. dry with materialdried over anhydrous MgSO4
  9. concentrationconcentrated in vacuo
  10. customThe residue was crystallized from EtOAc and n-hexane

Sources & evidence

ORD record
ord-104b755530b442f88d73722ca86c3649
Source dataset
uspto-grants-2008_12
Patent number
US07459451B2

Reaction notes

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