4-(benzyloxy)-6-(1-methyl-1H-pyrazol-4-yl)pyrazolo[1,5-a]pyridine → HCID 67374373, compound

HRID 1253543Notes

Reaction equation

HRID 1253543 reaction equation
C([O:8][C:9]1[C:10]2[N:11]([N:21]=[CH:22][CH:23]=2)[CH:12]=[C:13]([C:15]2[CH:16]=[N:17][N:18]([CH3:20])[CH:19]=2)[CH:14]=1)C1C=CC=CC=1>CCO.[OH-].[OH-].[Pd+2]>[CH3:20][N:18]1[CH:19]=[C:15]([C:13]2[CH:14]=[C:9]([OH:8])[C:10]3[N:11]([N:21]=[CH:22][CH:23]=3)[CH:12]=2)[CH:16]=[N:17]1

Participants

4

Reactant 1

HCID 673749564-(benzyloxy)-6-(1-methyl-1H-pyrazol-4-yl)pyrazolo[1,5-a]pyridine

Product 1

HCID 67374373HCID 67374373, compound

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalyst2×HCID 702EthanolSolvent

Procedure

4-(benzyloxy)-6-(1-methyl-1H-pyrazol-4-yl)pyrazolo[1,5-a]pyridine (185 mg, 0.608 mmol) and palladium hydroxide on carbon (85 mg, 0.122 mmol, 20 wt %) were suspended in EtOH (10 ml) and placed under an atmosphere of hydrogen (balloon). After 2 h, additional palladium hydroxide on carbon (85 mg, 0.122 mmol, 20 wt %) was added and the mixture was allowed to stir overnight. The reaction mixture was filtered through a 45 μm syringe filter and the filtrate was concentrated. The residue was purified by column chromatography on silica gel (methanol/ethyl acetate gradient) to afford 6-(1-methyl-1H-pyrazol-4-yl)pyrazolo[1,5-a]pyridin-4-ol.

Workup

  1. filtrationThe reaction mixture was filtered through a 45 μm syringe
  2. filtrationfilter
  3. concentrationthe filtrate was concentrated
  4. customThe residue was purified by column chromatography on silica gel (methanol/ethyl acetate gradient)

Sources & evidence

ORD record
ord-e3378b1708fb4106b12f6eb166928497
Source dataset
uspto-grants-2013_06
Patent number
US08455477B2

Reaction notes

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