HCID 59810835, compound → HCID 59810787, compound

HRID 2113703Notes

Reaction equation

HRID 2113703 reaction equation
[CH:1]1([N:6]2[C:14]3[C:9](=[CH:10][CH:11]=[C:12]([CH:15]([OH:17])[CH3:16])[CH:13]=3)[C:8]([CH2:18][CH3:19])=[N:7]2)[CH2:5][CH2:4][CH2:3][CH2:2]1.[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1>C(Cl)Cl>[CH:1]1([N:6]2[C:14]3[C:9](=[CH:10][CH:11]=[C:12]([C:15](=[O:17])[CH3:16])[CH:13]=3)[C:8]([CH2:18][CH3:19])=[N:7]2)[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

4

Reactant 2

HCID 59810835HCID 59810835, compoundHCID 178418287HCID 178418287, compound

Product 1

HCID 59810787HCID 59810787, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Into a 1-neck round-bottom flask was added 1-(1-cyclopentyl-3-ethyl-1H-indazol-6-yl)ethanol (1.06 g, 4.10 mmol), pyridinium chlorochromate (1.77 g, 8.20 mmol) and 40 mL of methylene chloride. The reaction was stirred at room temperature for 1 hour, filtered through Celite, and rinsed with 200 mL of ethyl acetate. Approximately 20 g of silica gel were added and the mixture was evaporated to dryness under reduced pressure. The residue was purified by column chromatography over silica gel eluting with 20% ethyl acetate in hexanes to yield 1-(1-cyclopentyl-3-ethyl-1H-indazol-6-yl)ethanone (809 mg, 77%).

Workup

  1. filtrationfiltered through Celite
  2. washrinsed with 200 mL of ethyl acetate
  3. additionApproximately 20 g of silica gel were added
  4. customthe mixture was evaporated to dryness under reduced pressure
  5. customThe residue was purified by column chromatography over silica gel eluting with 20% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-e87dfd4e5f844e5b93f77699e195aee1
Source dataset
uspto-grants-2008_10
Patent number
US07432266B2

Reaction notes

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