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

HRID 887744Notes

Reaction equation

HRID 887744 reaction equation
[CH3:1][O:2][C:3](=[O:20])/[CH:4]=[CH:5]/[C:6]1[CH:14]=[CH:13][C:12]2[C:8](=[CH:9][N:10]([CH3:15])[N:11]=2)[C:7]=1[C:16]([O:18][CH3:19])=[O:17]>CO.[C].[Pd]>[CH3:1][O:2][C:3](=[O:20])[CH2:4][CH2:5][C:6]1[CH:14]=[CH:13][C:12]2[C:8](=[CH:9][N:10]([CH3:15])[N:11]=2)[C:7]=1[C:16]([O:18][CH3:19])=[O:17]

Participants

4

Reactant 1

HCID 59145896methyl 5-[(1E)-3-methoxy-3-oxoprop-1-en-1-yl]-2-methyl-2H-indazole-4-carboxylate

Product 1

HCID 59145936methyl 5-(3-methoxy-3-oxopropyl)-2-methyl-2H-indazole-4-carboxylateYield 79.1%

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-methyl-2H-indazole-4-carboxylate (1.02 g, 3.72 mmol) in methanol (40 mL) was added palladium-carbon powder (100 mg), and the mixture was stirred under a hydrogen atmosphere at room temperature for 12 hr. The catalyst was filtered off, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate) to give the title compound (813 mg, yield 79%).

Workup

  1. filtrationThe catalyst was filtered off
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customThe residue was purified by silica gel column chromatography (ethyl acetate)

Sources & evidence

ORD record
ord-fa9f6b8f39484d32a76b17e5af1116d7
Source dataset
uspto-grants-2012_08
Patent number
US08247429B2

Reaction notes

Loading…