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Paper | Regular issue | Vol 53, No. 3, 2000, pp.665-673
Published online, 1st January, 1970
DOI: 10.3987/COM-99-8815
■ Synthesis of 5-Substituted Indole Derivatives, Part II. Synthesis of Sumatriptan through the Japp-Klingemann Reaction

Béla Pete,* István Bitter, Kálmán Harsányi, and László Tõke

*Organic Chemical Technology Research Group of the Hungarian Academy of Sciences at the Technical University of Budapest, H-1521 Budapest, Hungary

Abstract

Synthesis of selective 5-HT1B/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).