N-[2-(5-fluoro-2-methyl-6,7-dihydrocyclopenta[e]indazol-8(2H)-ylidene)ethyl]acetamide → N-[2-(5-fluoro-2-methyl-2,6,7,8-tetrahydrocyclopenta[e]indazol-8-yl)ethyl]acetamide

HRID 887821Notes

Reaction equation

HRID 887821 reaction equation
[F:1][C:2]1[C:3]2[CH2:14][CH2:13][C:12](=[CH:15][CH2:16][NH:17][C:18](=[O:20])[CH3:19])[C:4]=2[C:5]2[C:9]([CH:10]=1)=[N:8][N:7]([CH3:11])[CH:6]=2>CO.[C].[Pd]>[F:1][C:2]1[C:3]2[CH2:14][CH2:13][CH:12]([CH2:15][CH2:16][NH:17][C:18](=[O:20])[CH3:19])[C:4]=2[C:5]2[C:9]([CH:10]=1)=[N:8][N:7]([CH3:11])[CH:6]=2

Participants

4

Reactant 1

HCID 68701541N-[2-(5-fluoro-2-methyl-6,7-dihydrocyclopenta[e]indazol-8(2H)-ylidene)ethyl]acetamide

Product 1

HCID 25025109N-[2-(5-fluoro-2-methyl-2,6,7,8-tetrahydrocyclopenta[e]indazol-8-yl)ethyl]acetamideYield 77.4%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Procedure

To a solution of N-[2-(5-fluoro-2-methyl-6,7-dihydrocyclopenta[e]indazol-8(2H)-ylidene)ethyl]acetamide (82.0 mg, 0.300 mmol) in methanol (3 mL) was added palladium-carbon powder (8.2 mg), and the mixture was stirred under a hydrogen atmosphere at room temperature for 32 hr. The catalyst was filtered off, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (NH, methanol/ethyl acetate=0/100→5/95) to give the title compound (63.9 mg, yield 77%).

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 (NH, methanol/ethyl acetate=0/100→5/95)

Sources & evidence

ORD record
ord-c0695d7dc85e490d809fccd393ee36f4
Source dataset
uspto-grants-2012_08
Patent number
US08247429B2

Reaction notes

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