methyl 5-[(1E)-3-methoxy-3-oxoprop-1-en-1-yl]-2,3-dimethyl-2H-indazole-4-carboxylate → methyl 5-(3-methoxy-3-oxopropyl)-2,3-dimethyl-2H-indazole-4-carboxylate

HRID 887745Notes

Reaction equation

HRID 887745 reaction equation
[CH3:1][O:2][C:3](=[O:21])/[CH:4]=[CH:5]/[C:6]1[CH:14]=[CH:13][C:12]2[C:8](=[C:9]([CH3:16])[N:10]([CH3:15])[N:11]=2)[C:7]=1[C:17]([O:19][CH3:20])=[O:18]>CO.[C].[Pd]>[CH3:1][O:2][C:3](=[O:21])[CH2:4][CH2:5][C:6]1[CH:14]=[CH:13][C:12]2[C:8](=[C:9]([CH3:16])[N:10]([CH3:15])[N:11]=2)[C:7]=1[C:17]([O:19][CH3:20])=[O:18]

Participants

4

Reactant 1

HCID 59145912methyl 5-[(1E)-3-methoxy-3-oxoprop-1-en-1-yl]-2,3-dimethyl-2H-indazole-4-carboxylate

Product 1

HCID 59145916methyl 5-(3-methoxy-3-oxopropyl)-2,3-dimethyl-2H-indazole-4-carboxylateYield 91%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Procedure

To a solution of methyl 5-[(1E)-3-methoxy-3-oxoprop-1-en-1-yl]-2,3-dimethyl-2H-indazole-4-carboxylate (726 mg, 2.52 mmol) in methanol (25 mL) was added palladium-carbon powder (145 mg), and the mixture was stirred under a hydrogen atmosphere at room temperature for 18 hr. The catalyst was filtered off, and the filtrate was concentrated under reduced pressure to give the title compound (666 mg, yield 91%).

Workup

  1. filtrationThe catalyst was filtered off
  2. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-f84cd2f65f5d4802a5621bf7fa93aac0
Source dataset
uspto-grants-2012_08
Patent number
US08247429B2

Reaction notes

Loading…