Synthesis of 4,6-difluoro-5-hydroxy-(alpha-methyl)tryptamine and 4,6-difluoro-5-hydroxy-(beta-methyl)tryptamine as potential selective monoamine oxidase B inhibitors

Condensation of 4-nitro-1-pentanal and 4-nitropentanal 3-methylbutanal with 3,5-difluoro-4-methoxyphenylhydrazine afforded 4,6-difluoro-5-methoxy-3-(2 '-nitro)propylindole 4a and 4,6-difluoro-5-methoxy-3-(1'-methyl-2'-nitro)et hylindole 4b, respectively, in one step. Reduction of the nitro,group with lithium aluminum hydride followed by removal of the methyl ether with boron tribromide produced the title compounds. They were inactive as MAO B inhib itors. (C) 1998 Elsevier Science S.A. All rights reserved.