197580-86-2

Upstream product

• 85952-29-0 (4-nitro-phenyl)-methanesulfonic acid methylamide 
• 541-41-3 chloroformic acid ethyl ester 

Downstream Products

• 264909-33-3 ethyl 5-(dimethylamino)-2-[[4-[(N-ethoxycarbonyl-N-methylaminosulfonyl)methyl]phenyl]hydrazin-2-ylidene]pentanoate 
• 765252-40-2 C₁₁H₁₆N₂O₄S 

Relevant academic research and scientific papers

Synthesis of 5-substituted indole derivatives, I. An improved method for the synthesis of sumatriptan

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).