Heterocycles p. 1139 - 1149 (1998)
Update date:2022-08-05
Topics: Synthesis Substituted Indole derivatives Sumatriptan Improved method
Pete, Bela
Bitter, Istvan
Szantay Jr., Csaba
Schon, Istvan
Toke, Laszlo
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).
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Doi:10.1002/hlca.19800630618
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