Synthesis of 5-substituted indole derivatives, part II. Synthesis of sumatriptan through the Japp-Klingemann reaction

Béla Pete, István Bitter, Kálmán Harsányi, László Tõke

Research output: Contribution to journalArticle

17 Citations (Scopus)

Abstract

Synthesis of selective 5-HT(1B/1D) receptor agonist, sumatriptan (1) was accomplished through decarboxylation of 2-carboxy-3-[2-(dimethylamino)ethyl]- N-methyl-1H-indole-5-methanesulfonamide (2) in quinoline with copper powder. The preparation of the acid (2) was effected through the Japp-Klingemann method thus avoiding the need for the formation of hydrazine from diazonium salt. Attempted decarboxylation in N,N-dimethylacetamide resulted in the formation of the β-carboline (16).

Original languageEnglish
Pages (from-to)665-673
Number of pages9
JournalHeterocycles
Volume53
Issue number3
DOIs
Publication statusPublished - Mar 1 2000

    Fingerprint

ASJC Scopus subject areas

  • Analytical Chemistry
  • Pharmacology
  • Organic Chemistry

Cite this