197580-86-2Relevant articles and documents
Synthesis of 5-substituted indole derivatives, I. An improved method for the synthesis of sumatriptan
Pete, Bela,Bitter, Istvan,Szantay Jr., Csaba,Schon, Istvan,Toke, Laszlo
, p. 1139 - 1149 (2007/10/03)
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).