5-[5-(Allyl-methyl-amino)-pent-1-ynyl]-6-fluoro-2,3-dihydro-indole-1-carboxylic acid 4-chloro-phenyl ester → 6-Fluoro-5-[5-(methyl-propyl-amino)-pentyl]-2,3-dihydro-indole-1-carboxylic acid phenyl ester

Participants

Reaction Steps

Hydrogenolysis at atmospheric pressure of 5 mg (0.013 mmol) 5-[5-(Allyl-methyl-amino)-pent-1-ynyl]-6-fluoro-2,3-dihydro-indole-1-carboxylic acid 4-chloro-phenyl ester in 0.5 ml AcOH in the presence of 5 mg 10% Pd/C during 12 hrs, followed by filtration, evaporation of the AcOH, distribution of the residue between Et2O and 0.5 M NaOH, drying of the organic layer with Na2SO4, evaporation of the solvent and chromatograpy on silica gel with EtOAc/MeOH/NEt3 10:1:0.1 gave 3 mg (64%) of 6-Fluoro-5-[5-(methyl-propyl-amino)-pentyl]-2,3-dihydro-indole-1-carboxylic acid phenyl ester as a yellow oil, MS: 399 (MH+)

Provenance & Evidence