Synthesis of 5-substituted indole derivatives, I. An improved method for the synthesis of sumatriptan

Béla Pete, István Bitter, Csaba Szántay, István Schon, László Toke

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Abstract

An improved synthesis of sumatriptan (1b) via Fischer cyclization was achieved by introducing the ethoxycarbonyl group on the N-atom of the sulphonamide moiety in N-methyl-4-hydrazinobenzenemethanesulphonamide (7). As a result, substitution on the benzylic carbon of the indole nucleus could be avoided; however, formation of 1,1-bis-(indol-2-yl)-4-dimethylaminobutane-type by-product (19) was observed. The indolization procedure was optimized to suppress the unwanted side reaction. The N-protection of the sulphonamide moiety was found to be beneficial regarding the purification of the 3-[2-(dimethylamino)ethyl]-N-ethoxycarbonyl-N-methyl-1H-indole-5- methanesulphonamide (18).

Original languageEnglish
Pages (from-to)1139-1149
Number of pages11
JournalHeterocycles
Volume48
Issue number6
DOIs
Publication statusPublished - Jan 1 1998

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ASJC Scopus subject areas

  • Analytical Chemistry
  • Pharmacology
  • Organic Chemistry

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