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

HRID 887792Notes

Reaction equation

HRID 887792 reaction equation
[Cl: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>O1CCCC1.[Pt]>[Cl: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 59145923methyl 6-chloro-5-[(1E)-3-methoxy-3-oxoprop-1-en-1-yl]-2-methyl-2H-indazole-4-carboxylate

Product 1

HCID 59145878methyl 6-chloro-5-(3-methoxy-3-oxopropyl)-2-methyl-2H-indazole-4-carboxylateYield 66.4%

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 6-chloro-5-[(1E)-3-methoxy-3-oxoprop-1-en-1-yl]-2-methyl-2H-indazole-4-carboxylate (440 mg, 1.43 mmol) in tetrahydrofuran (10 mL) was added 5% platinum-activated carbon (88 mg), and the mixture was stirred under a hydrogen atmosphere at room temperature for 2 days. The catalyst was filtered off, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane=30/70→70/30) to give the title compound (295 mg, yield 66%).

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/hexane=30/70→70/30)

Sources & evidence

ORD record
ord-37a5b12b9453426aba269a9aa6a34e46
Source dataset
uspto-grants-2012_08
Patent number
US08247429B2

Reaction notes

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