209682-64-4

Basic information

• Product Name: 5-Ethyl-3-[[(2R)-1-Methyl-2-pyrrolidinyl]Methyl]-1H-indole
• Synonyms: 5-Ethyl-3-[[(2R)-1-Methyl-2-pyrrolidinyl]Methyl]-1H-indole
• CAS NO: 209682-64-4
• Molecular Formula: C16H21N2
• Molecular Weight: 241.35134
• Product Categories: Chiral Reagents, Impurities, Pharmaceuticals, Intermediates & Fine Chemicals
• Mol File: 209682-64-4.mol
• Article Data: 5

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 5-Ethyl-3-[[(2R)-1-Methyl-2-pyrrolidinyl]Methyl]-1H-indole(CAS DataBase Reference)
• NIST Chemistry Reference: 5-Ethyl-3-[[(2R)-1-Methyl-2-pyrrolidinyl]Methyl]-1H-indole(209682-64-4)
• EPA Substance Registry System: 5-Ethyl-3-[[(2R)-1-Methyl-2-pyrrolidinyl]Methyl]-1H-indole(209682-64-4)

Safety Data

• Hazardous Substances Data: 209682-64-4(Hazardous Substances Data)

Usage

Description

5-Ethyl-3-[[(2R)-1-Methyl-2-pyrrolidinyl]Methyl]-1H-indole is a chemical compound with a complex structure, characterized by its indole core and various substituents. It is an impurity found in Eletriptan, a medication used for the treatment of migraines.

Uses

Used in Pharmaceutical Industry:
5-Ethyl-3-[[(2R)-1-Methyl-2-pyrrolidinyl]Methyl]-1H-indole is used as an impurity in the production of Eletriptan (E505000), a serotonin 5-HT1B/1D receptor agonist. It is important to control the presence of this compound in the final product, as it can affect the safety, efficacy, and quality of the antimigraine agent.
In the context of Eletriptan, the compound serves as a byproduct during the synthesis process. The pharmaceutical industry focuses on minimizing the presence of this impurity to ensure the drug's effectiveness and to meet regulatory standards for purity and safety.

Upstream product

• 68742-28-9 5-ethyl-1H-indole 
• 143322-57-0 (R)-5-bromo-3-(N-methylpyrrolidine-2-ylmethyl)-1H-indole 
• 5535-48-8 PVS 
• 205369-12-6 (R)-1-acetyl-5-bromo-3-(N-methylpyrrolidin-2-ylmethyl)-1H-indole 
• 180637-88-1 (R)-1-acetyl-5-[2-(phenylsulfonyl)ethyenyl]-3-(N-methylpyrrolidin-2-ylmethyl)-1H-indole 
• 180637-89-2 (R)-5-[(2-phenylsulfonyl)ethenyl]-3-(N-methylpyrrolidine-2-ylmethyl)-1H-indole 

Relevant articles and documents

A Low Rhodium Content Smart Catalyst for Hydrogenation and Hydroformylation Reactions

Abstract: This paper describes the preparation, broad characterization and study of activity in hydrogenation and hydroformylation reactions of an easily produced 0.18% Rh/Al2O3. Analytical studies on fresh and recycled samples shed light on the smart properties of such catalyst. Results showed high activity as well as fine/excellent chemoselectivity or regioselectivity, characteristics that may suggest a wide range of applicability. Graphic Abstract: The low metal content catalyst 0.18% Rh/Al2O3 was very active in both hydrogenation and hydroformylation reactions so providing intermediates for valuable APIs, as Nabumetone and Eletriptan, and a fragrance with a fresh, green-floral smell, that recalls scent of lily of the valley.[Figure not available: see fulltext.]

Investigational study into the formation of methoxy derivative and other impurities during the optimization of eletriptan hydrobromide

During the process development of eletriptan hydrobromide, we have observed formation of an unknown impurity in the final product at enhanced levels which was identified as a methoxy substituted derivative on the side chain of the product. The present work involves detailed optimization studies directed toward the development of an efficient process for the commercial production of eletriptan hydrobromide substantially free from the methoxy impurity and other impurities.

5-ALKYL INDOLE COMPOUNDS

Described herein are compounds selective for the 5-HT 1D-like receptor, which have the general formula: STR1 wherein: R 1 is linear or branched loweralkyl;R 2 is selected from a group of Formula II, III, IV and V: STR2 R 3 is selected from H and loweralkyl; R 4 is selected from H and loweralkyl; One of R. sup. 5 and R 6 is H and the other is independently selected from H, loweralkoxy, loweralkyl and hydroxy; andn is 1-3; or a salt, solvate or hydrate thereof.Also described is the use of these compounds as pharmaceuticals to treat indications where stimulation of the 5-HT 1D-like receptor is implicated, such as migraine.