208464-41-9

Basic information

• Product Name: (S)-5-broMo-3-((1-Methylpyrrolidin-2-yl)Methyl)-1H-indole
• Synonyms: (S)-5-broMo-3-((1-Methylpyrrolidin-2-yl)Methyl)-1H-indole;5-bromo-3-[[(2S)-1-methyl-2-pyrrolidinyl]methyl]-1H-Indole
• CAS NO: 208464-41-9
• Molecular Formula: C14H17BrN2
• Molecular Weight: 293.20218
• Mol File: 208464-41-9.mol
• Article Data: 15

Chemical Properties

• Appearance: /
• Solubility: DCM, Methanol
• CAS DataBase Reference: (S)-5-broMo-3-((1-Methylpyrrolidin-2-yl)Methyl)-1H-indole(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-5-broMo-3-((1-Methylpyrrolidin-2-yl)Methyl)-1H-indole(208464-41-9)
• EPA Substance Registry System: (S)-5-broMo-3-((1-Methylpyrrolidin-2-yl)Methyl)-1H-indole(208464-41-9)

Safety Data

• Hazardous Substances Data: 208464-41-9(Hazardous Substances Data)

Usage

Description

(S)-5-broMo-3-((1-Methylpyrrolidin-2-yl)Methyl)-1H-indole, also known as 5-Bromo-3-[[(2S)-1-methyl-2-pyrrolidinyl]methyl]-1H-indole, is an organic compound that serves as a crucial intermediate in the synthesis of various pharmaceutical compounds. It is characterized by its indole structure, with a bromine atom at the 5th position and a methylpyrrolidinyl group attached to the 3rd position. (S)-5-broMo-3-((1-Methylpyrrolidin-2-yl)Methyl)-1H-indole plays a significant role in the development of drugs targeting specific receptors in the human body.

Uses

Used in Pharmaceutical Industry:
(S)-5-broMo-3-((1-Methylpyrrolidin-2-yl)Methyl)-1H-indole is used as an intermediate in the synthesis of ent-Eletriptan (E505005), which is an enantiomeric impurity of the serotonin 5-HT1B/1D receptor agonist Eletriptan (E505000). This application is crucial for the development of drugs that can effectively target and modulate the activity of serotonin receptors, which are involved in various physiological processes, including mood regulation, appetite, and pain perception.
In the synthesis of Eletriptan, (S)-5-broMo-3-((1-Methylpyrrolidin-2-yl)Methyl)-1H-indole serves as a key building block, allowing chemists to create the final drug product with the desired stereochemistry and biological activity. By controlling the enantiomeric purity of Eletriptan, the compound can be more effectively used in the treatment of migraines and other conditions related to serotonin receptor dysregulation.
Furthermore, the compound may also have potential applications in the development of other drugs targeting different receptors or biological pathways. Its unique structure and functional groups make it a versatile starting material for the synthesis of various pharmaceutical compounds, contributing to the advancement of novel therapeutic agents in the pharmaceutical industry.

Upstream product

• 199659-03-5 3-(N-benzyloxycarbonylpyrrolidin-2S-ylcarbonyl)-5-bromo-1H-indole 
• 1353991-68-0 (R)-2-(5-bromo-1H-indole-3-carbonyl)pyrrolidine-1-carboxylic acid phenyl ester 
• 1353991-67-9 (R)-2-chlorocarbonylpyrrolidine-1-carboxylic acid phenyl ester 
• 105370-80-7 (R)-pyrrolidine-1,2-dicarboxylic acid 1-phenyl ester 
• 1196663-29-2 5-bromo-3-{[(2R)-1-methylpyrrolidin-2-yl]methyl}-1H-indole ethanedioate 
• 143322-56-9 (R)-3-[(N-benzyloxycarbonylpyrrolidin-2-yl)carbonyl]-5-bromo-1H-indole 
• 61350-62-7 N-benzyloxycarbonyl-D-proline acid chloride 
• 6404-31-5 Z-D-proline 

Downstream Products

• 143322-58-1 eletriptan 
• 209682-64-4 (R)-3-[(1-methyl-2-pyrrolidinyl)-methyl]-5-ethyl-1H-indole 
• 208464-81-7 C₂₆H₂₈N₂O₂ 
• 208464-80-6 C₂₆H₂₈N₂O₂ 
• 208465-04-7 (S)-5-(1-aza-1-tert-butoxycarbonylcyclohex-3-en-4-yl)-3-[(N-methylpyrrolidin-2-yl)methyl]-1-benzoylindole 
• 209682-64-4 5-ethyl-3-{[1-methylpyrrolidin-2-yl]methyl}-1H-indole 
• 180637-89-2 (R)-5-[(2-phenylsulfonyl)ethenyl]-3-(N-methylpyrrolidine-2-ylmethyl)-1H-indole 
• 143322-55-8 (R)-3-(1-methyl-2-pyrrolidinylmethyl)-1H-indole 

Relevant articles and documents

PROCESS FOR PREPARING PURE 5-BROMO-3-[(R)-1-METHYL-PYRROLIDIN-2-YLMETHYL]-1H-INDOLE, INTERMEDIATE FOR ELETRIPTAN

Disclosed is a process for preparing pure 5-bromo-3-[(R)-1-methyl-pyrrolidin-2-ylmethyl]-1H-indole (BIP), an intermediate for eletriptan. The process comprises forming organic acid salt of BIP and then regenerating the said salt to give pure BIP.

PROCESS FOR THE PREPARATION OF 5-SUBSTSITUTED INDOLE DERIVATIVE

The present invention relates to an improved and industrially advantageous process for preparation of eletri tan of formula I,or pharmaceutically acceptable salts thereof from bromo indole intermediate of formula II, through isolation of N-acetylated bromo indole intermediate of formula III, to elude carrying forward of impurities to next stage. The present invention relates to process for the preparation of 5-bromo-3-[(R)-l-methyl-pyrrolidin-2- lmeth l -lH-indol of formula II, a key intermediate for the synthesis of eletriptan or pharmaceutically acceptable salts thereof, through novel keto carbamate intermediate. The present invention also relates to novel process for the preparation of a-form of eletriptan hydrobromide.

SYNTHESIS OF 3-{[(2R)-1-METHYLPYRROLIDIN-2-YL]METHYL}-5-[2-(PHENYLSULFONYL)ETHYL]-1H-INDOLE

The present invention refers to the synthesis of 3-{[(2R)-l-methylpyrrolidin-2-yl]methyl}-5-[2-(phenylsulfonyl)ethyl]-lH-indole, a drug known by the name Eletriptan, or of its salts. In particular, the present invention regards a process for the synthesis of Eletriptan or of its salt, comprising the following steps: a) Salifying the intermediate of Formula (6), using a dicarboxylic acid to obtain a derived salt; b) Optionally, purifying said raw salt obtained according to step a) by solvent crystallization to obtain a purified salt of the intermediate of Formula (6); c) Converting said salt of the intermediate of formula (6) according to step a) or said purified salt according to step b) into an intermediate of formula (10); d) Converting the intermediate of Formula (10) into Eletriptan or its salt.