4-(4-Benzyloxyphenyl)-6-(4-fluorophenyl)-2-methyl-5-(4-pyridyl)pyrazolo[3,4-b]pyridine → HCID 136367827, compound

HRID 42622Notes

Reaction equation

HRID 42622 reaction equation
C([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[C:16]3[C:17](=[N:34][N:35]([CH3:37])[CH:36]=3)[N:18]=[C:19]([C:27]3[CH:32]=[CH:31][C:30]([F:33])=[CH:29][CH:28]=3)[C:20]=2[C:21]2[CH:26]=[CH:25][N:24]=[CH:23][CH:22]=2)=[CH:11][CH:10]=1)C1C=CC=CC=1>CCO.[Pd]>[F:33][C:30]1[CH:31]=[CH:32][C:27]([C:19]2[C:20]([C:21]3[CH:26]=[CH:25][N:24]=[CH:23][CH:22]=3)=[C:15]([C:12]3[CH:11]=[CH:10][C:9]([OH:8])=[CH:14][CH:13]=3)[C:16]3[C:17](=[N:34][N:35]([CH3:37])[CH:36]=3)[N:18]=2)=[CH:28][CH:29]=1

Participants

4

Reactant 1

HCID 104355074-(4-Benzyloxyphenyl)-6-(4-fluorophenyl)-2-methyl-5-(4-pyridyl)pyrazolo[3,4-b]pyridine

Product 1

HCID 136367827HCID 136367827, compoundYield 76.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of 4-(4-benzyloxyphenyl)-6-(4-fluorophenyl)-2-methyl-5-(4-pyridyl)pyrazolo[3,4-b]pyridine (112 mg, 0.2 mmol, obtained in example 252) in EtOH (13 mL), 10% Pd/C (20 mg) was added and it was hydrogenated under atmospheric pressure at room temperature for 2 days. It was filtered through celite, washed with EtOH and concentrated. The crude product obtained was purified by chromatography on silica gel using hexane-EtOAc-MeOH mixtures of increasing polarity as eluent, to afford 61 mg of the title compound (yield: 67%)

Workup

  1. filtrationIt was filtered through celite
  2. washwashed with EtOH
  3. concentrationconcentrated
  4. customThe crude product obtained
  5. customwas purified by chromatography on silica gel
  6. temperatureof increasing polarity as eluent

Sources & evidence

ORD record
ord-f0eb2222979d442bbb64890606422b84
Source dataset
uspto-grants-2013_09
Patent number
US08536194B2

Reaction notes

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