4-(benzyloxy)-1-(2-cyclopropyl-3-methyl-2H-indazol-5-yl)pyridin-2(1H)-one → 1-(2-cyclopropyl-3-methyl-2H-indazol-5-yl)-4-hydroxypyridin-2(1H)-one

HRID 1497368Notes

Reaction equation

HRID 1497368 reaction equation
C([O:8][C:9]1[CH:14]=[CH:13][N:12]([C:15]2[CH:23]=[CH:22][C:21]3[C:17](=[C:18]([CH3:27])[N:19]([CH:24]4[CH2:26][CH2:25]4)[N:20]=3)[CH:16]=2)[C:11](=[O:28])[CH:10]=1)C1C=CC=CC=1>CO.[C].[Pd]>[CH:24]1([N:19]2[C:18]([CH3:27])=[C:17]3[C:21]([CH:22]=[CH:23][C:15]([N:12]4[CH:13]=[CH:14][C:9]([OH:8])=[CH:10][C:11]4=[O:28])=[CH:16]3)=[N:20]2)[CH2:25][CH2:26]1

Participants

4

Reactant 1

HCID 1177986944-(benzyloxy)-1-(2-cyclopropyl-3-methyl-2H-indazol-5-yl)pyridin-2(1H)-one

Product 1

HCID 1177986831-(2-cyclopropyl-3-methyl-2H-indazol-5-yl)-4-hydroxypyridin-2(1H)-oneYield 93.9%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Procedure

To a solution of 4-(benzyloxy)-1-(2-cyclopropyl-3-methyl-2H-indazol-5-yl)pyridin-2(1H)-one (256 mg) in methanol (5 ml) was added 10% palladium carbon (100 mg) at room temperature, and the mixture was stirred under a hydrogen atmosphere at the same temperature for 1 hr. The insoluble material was filtered off through celite, and the filtrate was concentrated under reduced pressure. The obtained residue was recrystallized from ethyl acetate to give the title compound (182 mg).

Workup

  1. filtrationThe insoluble material was filtered off through celite
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customThe obtained residue was recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-c29687161333469693afb30882da36a2
Source dataset
uspto-grants-2015_12
Patent number
US09199963B2

Reaction notes

Loading…