Ethylacetate methanol → {2-Ethyl-1-[1-(4-fluorobenzyl)-1H-1,2,4-triazol-5-yl]butyl}amine

HRID 748059Notes

Reaction equation

HRID 748059 reaction equation
[N:1]([CH:4]([C:10]1[N:14]([CH2:15][C:16]2[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=2)[N:13]=[CH:12][N:11]=1)[CH:5]([CH2:8][CH3:9])[CH2:6][CH3:7])=[N+]=[N-].CO.CCOC(C)=O>CCOC(C)=O.[Pd]>[CH2:8]([CH:5]([CH2:6][CH3:7])[CH:4]([NH2:1])[C:10]1[N:14]([CH2:15][C:16]2[CH:17]=[CH:18][C:19]([F:22])=[CH:20][CH:21]=2)[N:13]=[CH:12][N:11]=1)[CH3:9]

Participants

5

Reactant 2

HCID 21584119Ethylacetate methanolHCID 866000065-(1-Azido-2-ethylbutyl)-1-(4-fluorobenzyl)-1H-1,2,4-triazole

Product 1

HCID 68593905{2-Ethyl-1-[1-(4-fluorobenzyl)-1H-1,2,4-triazol-5-yl]butyl}amineYield 68%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent2×

Procedure

To a suspension of 5% Pd/C in EtOAc was added a solution of 5-(1-azido-2-ethylbutyl)-1-(4-fluorobenzyl)-1H-1,2,4-triazole in EtOAc and the mixture was shaken on a Parr apparatus for 2 h under 3 atm of H2. The mixture was filtered through Celite, washed several times with EtOAc, concentrated in vacuo, and purified by column chromatography (SiO2, EtOAc, then, MeOH/EtOAc, 1:9, then 1:4) to yield 68% of the amine.

Workup

  1. filtrationThe mixture was filtered through Celite
  2. washwashed several times with EtOAc
  3. concentrationconcentrated in vacuo
  4. custompurified by column chromatography (SiO2, EtOAc

Sources & evidence

ORD record
ord-dc75d4e9335e488fb5822c0b411d7cbf
Source dataset
uspto-grants-2008_07
Patent number
US07399778B2

Reaction notes

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