153654-26-3

Basic information

• Product Name: 3-[2-(dimethylamino)ethyl]-5-[(methylsulfamoyl)methyl]-1H-indole-2-carboxylic acid
• CAS NO: 153654-26-3
• Molecular Formula: C₁₅H₂₁N₃O₄S
• Molecular Weight: 339.4099
• Mol File: 153654-26-3.mol
• Article Data: 1

Chemical Properties

• Boiling Point: 587°C at 760 mmHg
• Flash Point: 308.8°C
• Density: 1.356g/cm³
• Vapor Pressure: 1.26E-14mmHg at 25°C
• Refractive Index: 1.626
• CAS DataBase Reference: 3-[2-(dimethylamino)ethyl]-5-[(methylsulfamoyl)methyl]-1H-indole-2-carboxylic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 3-[2-(dimethylamino)ethyl]-5-[(methylsulfamoyl)methyl]-1H-indole-2-carboxylic acid(153654-26-3)
• EPA Substance Registry System: 3-[2-(dimethylamino)ethyl]-5-[(methylsulfamoyl)methyl]-1H-indole-2-carboxylic acid(153654-26-3)

Safety Data

• Hazardous Substances Data: 153654-26-3(Hazardous Substances Data)

Upstream product

• 154064-62-7 3-[2-(dimethylamino)ethyl]-2-ethoxycarbonyl-N-methyl-1H-indole-5-methanesulfonamide 

Downstream Products

• 103628-46-2 sumatripan 

Relevant articles and documents

Synthesis of 5-substituted indole derivatives, part II. Synthesis of sumatriptan through the Japp-Klingemann reaction

Synthesis of selective 5-HT(1B/1D) receptor agonist, sumatriptan (1) was accomplished through decarboxylation of 2-carboxy-3-[2-(dimethylamino)ethyl]- N-methyl-1H-indole-5-methanesulfonamide (2) in quinoline with copper powder. The preparation of the acid (2) was effected through the Japp-Klingemann method thus avoiding the need for the formation of hydrazine from diazonium salt. Attempted decarboxylation in N,N-dimethylacetamide resulted in the formation of the β-carboline (16).