HCID 86602417, compound → HCID 69183957, compound

HRID 2373240Notes

Reaction equation

HRID 2373240 reaction equation
[CH2:1]([N:3]1[C:7]2=[N:8][C:9]([CH:26]([CH3:28])[CH3:27])=[C:10](/[CH:19]=[CH:20]/[C:21]([O:23][CH2:24][CH3:25])=[O:22])[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]>CO.CC(O)=O.[OH-].[Pd+2].[OH-]>[CH2:1]([N:3]1[C:7]2=[N:8][C:9]([CH:26]([CH3:28])[CH3:27])=[C:10]([CH2:19][CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22])[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

4

Reactant 1

HCID 86602417HCID 86602417, compound

Product 1

HCID 69183957HCID 69183957, compoundYield 45.7%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 10129899Acetic acid methanolSolvent

Procedure

A solution of ethyl (2E)-3-[1-ethyl-6-isopropyl-4-(5-methyl-3-pyridyl)-1H-pyrazolo[3,4-b]pyridin-5-yl]acrylate (268 mg) in MeOH-AcOH (90:10, 10 ml) was hydrogenated (3 atm) over palladium hydroxide (38 mg) at room temperature for 8 hours. The reaction mixture was filtered through celite pad and the filtrate was concentrated in vacuo. The residue was dissolved in EtOAc and washed with saturated aqueous NaHCO3, water, brine, dried over anhydrous MgSO4 and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel eluting with a mixture of EtOAc and n-hexane (1:2) to give ethyl 3-[1-ethyl-6-isopropyl-4-(5-methyl-3-pyridyl)-1H-pyrazolo[3,4-b]pyridin-5-yl]propanoate (123 mg) as a colorless oil.

Workup

  1. customat room temperature
  2. customfor 8 hours
  3. filtrationThe reaction mixture was filtered through celite pad
  4. concentrationthe filtrate was concentrated in vacuo
  5. dissolutionThe residue was dissolved in EtOAc
  6. washwashed with saturated aqueous NaHCO3, water, brine
  7. dry with materialdried over anhydrous MgSO4
  8. concentrationconcentrated in vacuo
  9. customThe residue was purified by flash column chromatography on silica gel eluting with a mixture of EtOAc and n-hexane (1:2)

Sources & evidence

ORD record
ord-81ae213a417e497caf9fecddc2d5c0c2
Source dataset
uspto-grants-2008_12
Patent number
US07459451B2

Reaction notes

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