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

HRID 573333Notes

Reaction equation

HRID 573333 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]([CH:24]([CH3:26])[CH3:25])[N:16]=2)=[N:13][CH:14]=1)C1C=CC=CC=1>CO.CCOC(C)=O.[Pd]>[CH3:26][CH: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 667278693-[5-(Benzyloxy)pyridin-2-yl]-1-(1-methylethyl)-1H-pyrazolo[4,3-b]pyridine

Product 1

HCID 1363976856-[1-(1-Methylethyl)-1H-pyrazolo[4,3-b]pyridin-3-yl]pyridin-3-olYield 86.6%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 3-[5-(benzyloxy)pyridin-2-yl]-1-(1-methylethyl)-1H-pyrazolo[4,3-b]pyridine (219 mg) and 10% Pd—C (50% wet, 73.1 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 (10 mL). The filtrate was concentrated under reduced pressure to give the title compound (140 mg).

Workup

  1. filtrationThe solid was filtrated
  2. washwashed with MeOH (10 mL)
  3. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-89ce2b6fe5974b69bad09c24aa5f733e
Source dataset
uspto-grants-2015_05
Patent number
US09029536B2

Reaction notes

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