3-[5-(Benzyloxy)pyridin-2-yl]-1-ethyl-1H-pyrazolo[4,3-b]pyridine → 6-(1-Ethyl-1H-pyrazolo[4,3-b]pyridin-3-yl)pyridin-3-ol

HRID 573325Notes

Reaction equation

HRID 573325 reaction equation
C([O:8][C:9]1[CH:10]=[CH:11][C:12]([C:15]2[C:19]3=[N:20][CH:21]=[CH:22][CH:23]=[C:18]3[N:17]([CH2:24][CH3:25])[N:16]=2)=[N:13][CH:14]=1)C1C=CC=CC=1>CO.CCOC(C)=O.[Pd]>[CH2:24]([N:17]1[C:18]2[C:19](=[N:20][CH:21]=[CH:22][CH:23]=2)[C:15]([C:12]2[N:13]=[CH:14][C:9]([OH:8])=[CH:10][CH:11]=2)=[N:16]1)[CH3:25]

Participants

5

Reactant 1

HCID 667280313-[5-(Benzyloxy)pyridin-2-yl]-1-ethyl-1H-pyrazolo[4,3-b]pyridine

Product 1

HCID 1363976906-(1-Ethyl-1H-pyrazolo[4,3-b]pyridin-3-yl)pyridin-3-olYield 84.1%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 3-[5-(benzyloxy)pyridin-2-yl]-1-ethyl-1H-pyrazolo[4,3-b]pyridine (224 mg) and 10% Pd—C (50% wet, 78 mg) in MeOH (3 mL) and AcOEt (3 mL) was hydrogenated under balloon pressure at room temperature overnight. The solid was filtrated and washed with MeOH (50 mL×3). The filtrate was concentrated under reduced pressure. The precipitate was collected by filtration and washed with 25% AcOEt in hexane to give the title compound (137 mg).

Workup

  1. filtrationThe solid was filtrated
  2. washwashed with MeOH (50 mL×3)
  3. concentrationThe filtrate was concentrated under reduced pressure
  4. filtrationThe precipitate was collected by filtration
  5. washwashed with 25% AcOEt in hexane

Sources & evidence

ORD record
ord-3e0f702e81204017a5a98ed8fd300d13
Source dataset
uspto-grants-2015_05
Patent number
US09029536B2

Reaction notes

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