894351-85-0

Usage

Chemical Properties

Off-White Solid

Uses

Intermediate for the preparation of Naratriptan and other

Upstream product

• 894351-84-9 2-(1-benzyl-1H-indol-5-yl)ethenesulfonic acid methylamide 
• 63263-84-3 N-benzylindoline-5-carboxaldehyde 
• 63263-88-7 1-benzyl-1H-indole-5-carbaldehyde 
• 1200070-42-3 2-(4-amino-3-iodo-phenyl)ethanesulfonic acid methylamide 
• 1268266-01-8 2-(4-benzylamino-3-ethynylphenyl)ethanesulfonic acid methylamide 
• 1268265-97-9 2-(4-benzylamino-3-trimethylsilanylethynyl-phenyl)ethanesulfonic acid methylamide 
• 1268265-93-5 2-(4-benzylamino-3-iodophenyl)ethanesulfonic acid methylamide 
• 98623-16-6 2-(4-amino-phenyl)ethanesulfonic acid methylamide 

Downstream Products

• 894351-86-1 2-[1-benzyl-3-(1-methyl-1,2,3,6-tetrahydro-pyridin-4-yl)-1H-indol-5-yl]-ethanesulfonic acid methylamide 
• 143388-64-1 naratriptan hydrochloride 
• 121679-13-8 naratriptan 
• 894351-87-2 N-methyl-2-[1-benzyl-3-(1-methylpiperidin-4-yl)-1H-indol-5-yl]ethanesulfonamide 

Relevant academic research and scientific papers

A PROCESS FOR THE SYNTHESIS OF NARATRIPTAN

The present invention relates to a process for preparing naratriptan or a salt thereof, the process comprising: (a) reacting a compound of formula (3) with a compound of the formula HCCR wherein Z is a protecting group, Y is a leaving group and R is a trialkyl silyl group, a trialkylstannyl group or a zinc (II) halide, to obtain the compound of formula (4); (b) converting the compound of formula (4) to a compound of formula (5) wherein Z'' is hydrogen or a benzyl group; (c) converting the compound of formula (5) to naratriptan; and (d) optionally converting naratriptan to a salt thereof. The present invention also provides novel compounds (3) and (4) and processes for their preparation.

New synthesis of naratriptan

A new synthesis of N-methyl-3-(1-methyl-4-piperidinyl)-1H-indole-5-ethanesulfonamide (naratriptan, 1a) has been elaborated starting from 1-benzyl-1H-indole-5-carbaldehyde (14b). The 1-benzyl group proved to be an advantageous protecting group in the course of the construction of the ethanesulfonamide and methylpipieridinyl side-chains and it was removed in the last step of the synthesis.{A figure is presented}.