반응 #44912

반응 방정식

5-benzyloxy-2-methyl-1-phenyl-1H-indole-3-carboxylic acid, 3,4-difluoro-benzylamide

Compound 56

5-benzyloxy-2-methyl-1-phenyl-1H-indole-3-carboxylic acid, 3,4-difluoro-benzylamide

→

5-hydroxy-2-methyl-1-phenyl-1H-indole-3-carboxylic acid, 3,4-difluorobenzylamide

수율 92.0%

용매

methanol

반응 조건

후처리

1. 1
   기타was degassed with argon for 10 min
2. 2
   workup.ADDITIONwas added 10% palladium on carbon (0.17 g)
3. 3
   여과The reaction was then filtered
4. 4
   농축concentrated under reduced pressure
5. 5
   기타the crude product residue was purified by flash column chromatography on silica gel (30% EtOAc-hexanes)

실험 절차

To a mixture of 5-benzyloxy-2-methyl-1-phenyl-1H-indole-3-carboxylic acid, 3,4-difluoro-benzylamide (Compound 56, 0.15 g, 0.31 mmol) in methanol (15 ml), which was degassed with argon for 10 min, was added 10% palladium on carbon (0.17 g), with continued degassing. The reaction was placed in par tube on hydrogenator and hydrogenated at 45 psi for 18 h. The reaction was then filtered, concentrated under reduced pressure and the crude product residue was purified by flash column chromatography on silica gel (30% EtOAc-hexanes) to yield 5-hydroxy-2-methyl-1-phenyl-1H-indole-3-carboxylic acid, 3,4-difluorobenzylamide (Compound 29) as a solid (0.11 g, 92%).

출처