205369-12-6

Basic information

• Product Name: (R)-N-Acetyl-5-bromo-3-(N-methylpyrrolidin-2-ylmethyl)-1H-indole
• Synonyms: (R)-N-Acetyl-5-bromo-3-(N-methylpyrrolidin-2-ylmethyl)-1H-indole;1-acetyl-5-bromo-3-{[(2R)-1-methylpyrrolidin-2-yl]methyl}-1H-indole;(R)-1-(5-Bromo-3-((1-methylpyrrolidin-2-yl)methyl)-1H-indol-1-yl)ethanone;1-(5-bromo-3-((1-methylpyrrolidin-2-yl)methyl)-1H-indol-1-yl)ethanone;1-[5-bromo-3-[[(2R)-1-methylpyrrolidin-2-yl]methyl]indol-1-yl]ethanone;(R)-1-acetyl-5-bromo-3-(N-methylpyrrolidin-2-ylmethyl)-1H-indole
• CAS NO: 205369-12-6
• Molecular Formula: C₁₆H₁₉BrN₂O
• Molecular Weight: 335.243
• Mol File: 205369-12-6.mol

Chemical Properties

• Boiling Point: 424.416 °C at 760 mmHg
• Flash Point: 210.479 °C
• Appearance: /
• Density: 1.43
• Storage Temp.: 2-8°C
• CAS DataBase Reference: (R)-N-Acetyl-5-bromo-3-(N-methylpyrrolidin-2-ylmethyl)-1H-indole(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-N-Acetyl-5-bromo-3-(N-methylpyrrolidin-2-ylmethyl)-1H-indole(205369-12-6)
• EPA Substance Registry System: (R)-N-Acetyl-5-bromo-3-(N-methylpyrrolidin-2-ylmethyl)-1H-indole(205369-12-6)

Safety Data

• Hazardous Substances Data: 205369-12-6(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Research:
(R)-N-Acetyl-5-bromo-3-(N-methylpyrrolidin-2-ylmethyl)-1H-indole is used as a research compound for exploring its potential applications in the treatment of various diseases and conditions. Its unique structure and biological activities are of interest to scientists in the field of medicinal chemistry, who are investigating its possible therapeutic effects and mechanisms of action.
Used in Medicinal Chemistry Development:
In the field of medicinal chemistry, (R)-N-Acetyl-5-bromo-3-(N-methylpyrrolidin-2-ylmethyl)-1H-indole serves as a starting point for the design and synthesis of new drugs. Its potential pharmacological properties make it a valuable target for further research and development, with the aim of creating novel therapeutic agents that can address unmet medical needs.
Used in Drug Discovery:
(R)-N-Acetyl-5-bromo-3-(N-methylpyrrolidin-2-ylmethyl)-1H-indole is employed in drug discovery processes to identify and optimize lead compounds with potential therapeutic benefits. Its unique chemical structure and biological activities provide a foundation for the development of new drugs that can target specific disease pathways or mechanisms.
Used in Preclinical Studies:
As a part of the drug development pipeline, (R)-N-Acetyl-5-bromo-3-(N-methylpyrrolidin-2-ylmethyl)-1H-indole is used in preclinical studies to evaluate its safety, efficacy, and pharmacokinetic properties. These studies are crucial for understanding the compound's potential as a therapeutic agent and for guiding its further development.

Upstream product

• 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 
• 61350-62-7 N-benzyloxycarbonyl-D-proline acid chloride 
• 6404-31-5 Z-D-proline 
• 143322-56-9 (R)-3-[(N-benzyloxycarbonylpyrrolidin-2-yl)carbonyl]-5-bromo-1H-indole 
• 143322-57-0 (R)-5-bromo-3-(N-methylpyrrolidine-2-ylmethyl)-1H-indole 
• 1196663-29-2 5-bromo-3-{[(2R)-1-methylpyrrolidin-2-yl]methyl}-1H-indole ethanedioate 
• 108-24-7 acetic anhydride 

Downstream Products

• 177834-92-3 eletriptan hydrobromide 
• 180637-89-2 (R)-5-[(2-phenylsulfonyl)ethenyl]-3-(N-methylpyrrolidine-2-ylmethyl)-1H-indole 
• 143322-58-1 eletriptan 
• 180637-88-1 (R)-1-acetyl-5-[2-(phenylsulfonyl)ethyenyl]-3-(N-methylpyrrolidin-2-ylmethyl)-1H-indole 
• 1408337-90-5 4-methyl-8-[2-(phenylsulfonyl)ethyl]-1,2,3,5,10,10a-hexahydropyrrolidino[3,2-b]indol-4-ium 
• 1408337-89-2 (R)-3-[(1-methyl-2-pyrrolidinyl)methyl]-5-[2-(phenylsulfonyl)-1-methoxyethyl]-1H-indole 
• 209682-64-4 5-ethyl-3-{[1-methylpyrrolidin-2-yl]methyl}-1H-indole 

Relevant articles and documents

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.

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.

Synthesis of compounds related to the anti-migraine drug eletriptan hydrobromide

Eletriptan hydrobromide (1) is a selective serotonin (5-HT1) agonist, used for the acute treatment of the headache phase of migraine attacks. During the manufacture of eletriptan hydrobromide the formation of various impurities were observed and identified by LC-MS. To control the formation of these impurities during the preparation of active pharmaceutical ingredients, the structure of the impurities must be known. Major impurities of the eletriptan hydrobromide synthesis were prepared and characterized by using various spectroscopic techniques, i.e., mass spectroscopy, FTIR , 1H NMR, 13C NMR/DEPT, and further confirmed by co-injection in HPLC. The present study will be of great help in the synthesis of highly pure eletriptan hydrobromide related compounds.

SYNTHESIS OF 3--5-[2-(PHENYLSULFONYL)ETHYL]-1H-INDOLE

The present invention refers to the synthesis of 3-{[(2R)-1-methylpyrrolidin-2-yl]methyl}-5-[2-(phenylsulfonyl)ethyl]-1H-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.

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.