methyl 6-fluoro-5-[(1E)-3-methoxy-3-oxoprop-1-en-1-yl]-2-methyl-2H-indazole-4-carboxylate → methyl 6-fluoro-5-(3-methoxy-3-oxopropyl)-2-methyl-2H-indazole-4-carboxylate

HRID 887784Notes

Reaction equation

HRID 887784 reaction equation
[F:1][C:2]1[C:3](/[CH:16]=[CH:17]/[C:18]([O:20][CH3:21])=[O:19])=[C:4]([C:12]([O:14][CH3:15])=[O:13])[C:5]2[C:9]([CH:10]=1)=[N:8][N:7]([CH3:11])[CH:6]=2>C1COCC1.CO.[C].[Pd]>[F:1][C:2]1[C:3]([CH2:16][CH2:17][C:18]([O:20][CH3:21])=[O:19])=[C:4]([C:12]([O:14][CH3:15])=[O:13])[C:5]2[C:9]([CH:10]=1)=[N:8][N:7]([CH3:11])[CH:6]=2

Participants

4

Reactant 1

HCID 59145866methyl 6-fluoro-5-[(1E)-3-methoxy-3-oxoprop-1-en-1-yl]-2-methyl-2H-indazole-4-carboxylate

Product 1

HCID 59145903methyl 6-fluoro-5-(3-methoxy-3-oxopropyl)-2-methyl-2H-indazole-4-carboxylateYield 94%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 21899815MeOH tetrahydrofuranSolvent

Procedure

To a solution of methyl 6-fluoro-5-[(1E)-3-methoxy-3-oxoprop-1-en-1-yl]-2-methyl-2H-indazole-4-carboxylate (430 mg, 21.47 mmol) in THF/methanol (5 mL/5 mL) was added palladium-carbon powder (86 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 (407 mg, yield 94%).

Workup

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

Sources & evidence

ORD record
ord-927855dd385a418db28dc78cf27b5c3d
Source dataset
uspto-grants-2012_08
Patent number
US08247429B2

Reaction notes

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