3-[4-(Benzyloxy)phenyl]-6-fluoro-1-(1-methylethyl)-1H-pyrazolo[4,3-b]pyridine → 4-[6-Fluoro-1-(1-methylethyl)-1H-pyrazolo[4,3-b]pyridin-3-yl]phenol

HRID 573354Notes

Reaction equation

HRID 573354 reaction equation
C([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[C:19]3=[N:20][CH:21]=[C:22]([F:24])[CH:23]=[C:18]3[N:17]([CH:25]([CH3:27])[CH3:26])[N:16]=2)=[CH:11][CH:10]=1)C1C=CC=CC=1>CCO.[Pd]>[F:24][C:22]1[CH:23]=[C:18]2[N:17]([CH:25]([CH3:27])[CH3:26])[N:16]=[C:15]([C:12]3[CH:11]=[CH:10][C:9]([OH:8])=[CH:14][CH:13]=3)[C:19]2=[N:20][CH:21]=1

Participants

4

Reactant 1

HCID 667282723-[4-(Benzyloxy)phenyl]-6-fluoro-1-(1-methylethyl)-1H-pyrazolo[4,3-b]pyridine

Product 1

HCID 1364090924-[6-Fluoro-1-(1-methylethyl)-1H-pyrazolo[4,3-b]pyridin-3-yl]phenolYield 77.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of 3-[4-(benzyloxy)phenyl]-6-fluoro-1-(1-methylethyl)-1H-pyrazolo[4,3-b]pyridine (130 mg) and 10% Pd—C (100 mg) in EtOH (20 mL) was stirred at room temperature for 1 h under H2 atmosphere, filtered and evaporated. The residue was purified by silica gel column chromatography (hexane/AcOEt) to give the title compound (76 mg).

Workup

  1. filtrationfiltered
  2. customevaporated
  3. customThe residue was purified by silica gel column chromatography (hexane/AcOEt)

Sources & evidence

ORD record
ord-0f6c5d4fac7f43ca8f2e63f5eac2759b
Source dataset
uspto-grants-2015_05
Patent number
US09029536B2

Reaction notes

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