Potassium Hydroxide → 2-[4,6-Bis(4-fluorophenyl)-5-(4-pyridyl)pyrazolo[3,4-b]pyridin-2-yl]acetic acid

HRID 42576Notes

Reaction equation

HRID 42576 reaction equation
[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][C:31]([O:33]CC)=[O:32])[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.[OH-].[K+]>CCO.O>[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][C:31]([OH:33])=[O:32])[CH:29]=3)[N:11]=[C:12]([C:20]3[CH:21]=[CH:22][C:23]([F:26])=[CH:24][CH:25]=3)[C:13]=2[C:14]2[CH:19]=[CH:18][N:17]=[CH:16][CH:15]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 67014566HCID 67014566, compound

Product 1

HCID 670143832-[4,6-Bis(4-fluorophenyl)-5-(4-pyridyl)pyrazolo[3,4-b]pyridin-2-yl]acetic acidYield 66%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a solution of ethyl 2-[4,6-bis(4-fluorophenyl)-5-(4-pyridyl)pyrazolo[3,4-b]pyridin-2-yl]acetate (0.09 g, 0.2 mmol, obtained in example 32) in EtOH (4.2 mL), a solution of KOH (0.09 g, 2.5 mmol) in water (0.5 mL) was added. This was heated to reflux for 1 h. It was allowed to cool and concentrated. The residue was dissolved in a mixture of EtOAc and water. The phases were separated. The aqueous phase was acidified and extracted with EtOAc. The combined organic phases were dried over Na2SO4 and concentrated to dryness, to afford 57 mg of title compound (yield: 66%).

Workup

  1. temperatureThis was heated
  2. temperatureto reflux for 1 h
  3. temperatureto cool
  4. concentrationconcentrated
  5. dissolutionThe residue was dissolved in a mixture of EtOAc and water
  6. customThe phases were separated
  7. extractionextracted with EtOAc
  8. dry with materialThe combined organic phases were dried over Na2SO4
  9. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-49040e64fcfd400e89cb671a23c34d54
Source dataset
uspto-grants-2013_09
Patent number
US08536194B2

Reaction notes

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