[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]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.
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