HCID 86657055, compound → HCID 123764692, compound

HRID 1253553Notes

Reaction equation

HRID 1253553 reaction equation
C([O:8][C:9]1[CH:10]=[C:11]([NH:18][C:19](=[O:25])[O:20][C:21]([CH3:24])([CH3:23])[CH3:22])[C:12]2[N:13]([N:15]=[CH:16][CH:17]=2)[CH:14]=1)C1C=CC=CC=1>C(O)C.[Pd]>[OH:8][C:9]1[CH:10]=[C:11]([NH:18][C:19](=[O:25])[O:20][C:21]([CH3:23])([CH3:22])[CH3:24])[C:12]2[N:13]([N:15]=[CH:16][CH:17]=2)[CH:14]=1

Participants

4

Reactant 1

HCID 86657055HCID 86657055, compound

Product 1

HCID 123764692HCID 123764692, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

tert-butyl [6-(benzyloxy)pyrazolo[1,5-a]pyridin-4-yl]carbamate from Step 3 (140 mg, 0.363 mmol) was dissolved in absolute ethanol (5 ml). Palladium on carbon (77 mg, 0.073 mmol) was added and the mixture was placed under an atmosphere of hydrogen (balloon). After 1 h, the mixture was filtered through a 45 μm syringe filter and the filtrate was concentrated. The residue was purified by column chromatography on silica gel (ethyl acetate/isohexane gradient) to afford tert-butyl (6-hydroxypyrazolo[1,5-a]pyridin-4-yl)carbamate.

Workup

  1. filtrationthe 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 (ethyl acetate/isohexane gradient)

Sources & evidence

ORD record
ord-306ed19e7f9145a0908faa3d2f0fee3d
Source dataset
uspto-grants-2013_06
Patent number
US08455477B2

Reaction notes

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