98623-50-8

Basic information

• Product Name: N-Methyl-1H-Indole-5-EthaneSulphonamide
• Synonyms: N-Methyl-1H-Indole-5-EthaneSulphonamide;N-Methyl-1H-indole-5-ethanesulfonamide;2-(1H-indol-5-yl)-N-MethylethanesulfonaMide;N-Methyl-1H-indole-5-ethanesulfonamide, >=98%;N-Methyl-1H-Indole-5-EthaneSulphomide
• CAS NO: 98623-50-8
• Molecular Formula: C11H14N2O2S
• Molecular Weight: 238.30606
• EINECS: 1592732-453-0
• Mol File: 98623-50-8.mol
• Article Data: 7

Chemical Properties

• Boiling Point: 458.4 °C at 760 mmHg
• Flash Point: 231 °C
• Appearance: /
• Density: 1.316g/cm³
• Vapor Pressure: 1.37E-08mmHg at 25°C
• Refractive Index: 1.632
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• Solubility: DMSO (Slightly), Methanol (Slightly)
• PKA: 11.52±0.40(Predicted)
• CAS DataBase Reference: N-Methyl-1H-Indole-5-EthaneSulphonamide(CAS DataBase Reference)
• NIST Chemistry Reference: N-Methyl-1H-Indole-5-EthaneSulphonamide(98623-50-8)
• EPA Substance Registry System: N-Methyl-1H-Indole-5-EthaneSulphonamide(98623-50-8)

Safety Data

• Hazardous Substances Data: 98623-50-8(Hazardous Substances Data)

Usage

Description

N-Methyl-1H-Indole-5-EthaneSulphonamide is an organic compound that serves as a crucial intermediate in the synthesis of pharmaceuticals. It is characterized by its unique molecular structure, which includes an indole ring and an ethane sulfonamide group. N-Methyl-1H-Indole-5-EthaneSulphonamide plays a significant role in the development of medications for various therapeutic applications.

Uses

Used in Pharmaceutical Industry:
N-Methyl-1H-Indole-5-EthaneSulphonamide is used as a key reagent in the synthesis of Naratriptan Hydrochloride (N378730), a triptan drug specifically designed for the treatment of migraine headaches. Triptans are known for their ability to alleviate migraine symptoms by constricting blood vessels and reducing inflammation. As a reagent, N-Methyl-1H-Indole-5-EthaneSulphonamide contributes to the production of this effective medication, helping to improve the quality of life for those who suffer from migraines.

InChI:InChI=1/C11H14N2O2S/c1-12-16(14,15)7-5-9-2-3-11-10(8-9)4-6-13-11/h2-4,6,8,12-13H,5,7H2,1H3

Upstream product

• 1190200-23-7 phenyl 2-(1H-indol-5-yl)ethanesulfonate 
• 74-89-5 methylamine 
• 1305334-90-0 2-(1H-indol-5-yl)-N-methyl ethenesulfonamide 
• 157835-85-3 1,1-dimethylethyl 3-ethenyl-1H-indole-1-carboxylate 
• 53654-36-7 3-vinyl-1H-indole 
• 1200070-42-3 2-(4-amino-3-iodo-phenyl)ethanesulfonic acid methylamide 
• 1268265-99-1 N-[2-ethynyl-4-(2-(methylsulfamoyl)ethyl)phenyl]acetamide 
• 1268265-95-7 N-[4-(2-{methylsulfamoyl}ethyl)-2-{2-(trimethylsilanyl)ethynyl}phenyl]acetamide 
• 1268265-90-2 N-[2-iodo-4-(2-(methylsulfamoyl)ethyl)phenyl]acetamide 
• 98623-16-6 2-(4-amino-phenyl)ethanesulfonic acid methylamide 
• 1204192-94-8 2-(3-phenylsulfanyl-1H-indol-5-yl)ethanesulfonicacid methylamide 
• 1025797-51-6 5-[2-(methylsulfamoyl)ethyl]-1H-indole-2-carboxylic acid 

Downstream Products

• 121679-20-7 N-methyl-2-(3-(1-methyl-1,2,3,6-tetrahydropyridin-4-yl)-1H-indol-5-yl)ethane-1-sulfonamide 
• 143388-64-1 naratriptan hydrochloride 
• 121679-13-8 naratriptan 

Relevant articles and documents

The photoredox-catalyzed hydrosulfamoylation of styrenes and its application in the novel synthesis of naratriptan

The hydrosulfamoylation of diverse aryl olefins provides facile access to alkylsulfonamides. Here we report a novel protocol utilizing radical-mediated addition and a thiol-assisted strategy to achieve the hydrosulfamoylation of diverse styrenes in modest to excellent yields under mild and economic reaction conditions. The methodology was found to provide an efficient and convenient approach for the synthesis of the anti-migraine drug naratriptan and it also can be used for the late-stage functionalization of natural products or medicines.

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.

PROCESS FOR PREPARATION OF NARATRIPTAN HYDROCHLORIDE

The present invention relates to an improved process for the preparation of N-methyl-3- (1-methyl-4-piperidinyl)-1H-indole-5-ethanesulfonamide hydrochloride of formula (I) having less than 0.15 % area by HPLC of 3-(1-methyl-4-piperidinyl)-1H-indole-5- ethanesulfonamide (1A) and intermediates thereof.