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

HRID 887800Notes

Reaction equation

HRID 887800 reaction equation
[CH3:1][N:2]1[CH:10]=[C:9]2[C:4]([CH:5]=[CH:6][C:7]3[CH2:13][CH2:12][C:11](=[CH:14][CH2:15][NH:16][C:17](=[O:19])[CH3:18])[C:8]=32)=[N:3]1>CO.[C].[Pd]>[CH3:1][N:2]1[CH:10]=[C:9]2[C:4]([CH:5]=[CH:6][C:7]3[CH2:13][CH2:12][CH:11]([CH2:14][CH2:15][NH:16][C:17](=[O:19])[CH3:18])[C:8]=32)=[N:3]1

Participants

4

Reactant 1

HCID 68700363N-[2-(2-methyl-6,7-dihydrocyclopenta[e]indazol-8(2H)-ylidene)ethyl]acetamide

Product 1

HCID 59145872N-[2-(2-methyl-2,6,7,8-tetrahydrocyclopenta[e]indazol-8-yl)ethyl]acetamideYield 73%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Procedure

To a solution of N-[2-(2-methyl-6,7-dihydrocyclopenta[e]indazol-8(2H)-ylidene)ethyl]acetamide (311 mg, 1.22 mmol) in methanol (12 mL) was added palladium-carbon powder (31 mg), and the mixture was stirred under a hydrogen atmosphere at room temperature for 3 hr. The catalyst was filtered off, and the filtrate was concentrated under reduced pressure and purified by silica gel column chromatography (methanol/ethyl acetate=0/100→25/75) to give the title compound (229 mg, yield 73%).

Workup

  1. filtrationThe catalyst was filtered off
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. custompurified by silica gel column chromatography (methanol/ethyl acetate=0/100→25/75)

Sources & evidence

ORD record
ord-e5fa874ded9f4d36865ffc7974d20fb9
Source dataset
uspto-grants-2012_08
Patent number
US08247429B2

Reaction notes

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