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Paper | Regular issue | Vol 48, No. 6, 1998, pp.1139-1149
Published online, 1st January, 1970
DOI: 10.3987/COM-97-8087
Synthesis of 5-Substituted Indole Derivatives, I. An Improved Method for the Synthesis of Sumatriptan

Béla Pete, István Bitter, Csaba Szántay, Jr., István Schön, and László Töke*

*Department of Organic Chemical Technology, Technical University Budapest, H-1521 Budapest, Gellért tér 4, Hungary

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).