143322-57-0

Basic information

• Product Name: (R)-5-Bromo-3-((1-methylpyrrolidin-2-yl)methyl)-1H-indole
• Synonyms: 5-BROMO-3-(1-METHYL PYRROLIDIN-2-YL METHYL)-1H-INDOLE;1H-Indole,5-broMo-3-[[(2R)-1-Methyl-2-pyrrolidinyl]Methyl]-;5-Bromo-3-(1-Methylpyrrolidin-2(R)-ylmethyl)-1H-Indole;5-bromo-3-[[(2R)-1-methyl-2-pyrrolidinyl]methyl]-1H-Indole;Eletriptan intermediate 2;(R)-5-Bromo-3-((1-methylpyrrolidin-2-yl)methyl)-1H-indole;5-Bromo-3-[((2R)-1-methylpyrrolidin-2-yl)methyl]-1H-indole;Eletriptan intermediate
• CAS NO: 143322-57-0
• Molecular Formula: C₁₄H₁₇BrN₂
• Molecular Weight: 293.2
• EINECS: 422-390-5
• Product Categories: Pharmaceutical material and intermeidates;API intermediates;Chiral Reagents;Indole Derivatives;Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 143322-57-0.mol
• Article Data: 15

Chemical Properties

• Boiling Point: 412.9 °C at 760 mmHg
• Flash Point: 203.5 °C
• Appearance: /
• Density: 1.418 g/cm³
• Vapor Pressure: 5E-07mmHg at 25°C
• Refractive Index: 1.655
• Storage Temp.: 2-8°C
• PKA: 16.28±0.30(Predicted)
• CAS DataBase Reference: (R)-5-Bromo-3-((1-methylpyrrolidin-2-yl)methyl)-1H-indole(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-5-Bromo-3-((1-methylpyrrolidin-2-yl)methyl)-1H-indole(143322-57-0)
• EPA Substance Registry System: (R)-5-Bromo-3-((1-methylpyrrolidin-2-yl)methyl)-1H-indole(143322-57-0)

Safety Data

• Hazard Codes: T,N
• Statements: 20/22-39-41-43-48/25-62-50/53
• Safety Statements: 53-45-60-61
• Hazardous Substances Data: 143322-57-0(Hazardous Substances Data)

Usage

Description

(R)-5-Bromo-3-((1-methylpyrrolidin-2-yl)methyl)-1H-indole is a chiral, halogenated indole derivative featuring a bromine atom at the 5th position and a 1-methylpyrrolidin-2-ylmethyl group at the 3rd position. (R)-5-Bromo-3-((1-methylpyrrolidin-2-yl)methyl)-1H-indole is characterized by its light brown solid appearance and is known for its unique chemical properties and potential applications in various fields.

Uses

Used in Pharmaceutical Industry:
(R)-5-Bromo-3-((1-methylpyrrolidin-2-yl)methyl)-1H-indole is used as an intermediate compound for the synthesis of various pharmaceuticals. Its unique structure allows it to be a key component in the development of new drugs targeting specific receptors or biological pathways.
Used in Chemical Research:
As a halogenated indole derivative, (R)-5-Bromo-3-((1-methylpyrrolidin-2-yl)methyl)-1H-indole is used as a research compound in the field of organic chemistry. It can be employed to study the effects of structural modifications on the biological activity of indole-based molecules and to explore new synthetic routes and methodologies.
Used in Drug Synthesis:
(R)-5-Bromo-3-((1-methylpyrrolidin-2-yl)methyl)-1H-indole is used as a building block in the synthesis of various drugs, particularly those targeting the serotonin 5-HT1B/1D receptors. It can be utilized to create novel therapeutic agents for the treatment of conditions such as migraine headaches, as seen in the case of Eletriptan.
Used in Material Science:
The unique structural features of (R)-5-Bromo-3-((1-methylpyrrolidin-2-yl)methyl)-1H-indole may also find applications in the field of material science, where it could be used to develop new materials with specific properties, such as optoelectronic devices or sensors.

InChI:InChI=1/C14H17BrN2/c1-17-6-2-3-12(17)7-10-9-16-14-5-4-11(15)8-13(10)14/h4-5,8-9,12,16H,2-3,6-7H2,1H3/t12-/m1/s1

Upstream product

• 1196663-29-2 5-bromo-3-{[(2R)-1-methylpyrrolidin-2-yl]methyl}-1H-indole ethanedioate 
• 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 

Downstream Products

• 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 
• 177834-92-3 eletriptan hydrobromide 
• 205369-12-6 (R)-1-acetyl-5-bromo-3-(N-methylpyrrolidin-2-ylmethyl)-1H-indole 
• 143322-58-1 eletriptan 
• 209682-64-4 (R)-3-[(1-methyl-2-pyrrolidinyl)-methyl]-5-ethyl-1H-indole 
• 1408337-89-2 (R)-3-[(1-methyl-2-pyrrolidinyl)methyl]-5-[2-(phenylsulfonyl)-1-methoxyethyl]-1H-indole 
• 1408337-90-5 4-methyl-8-[2-(phenylsulfonyl)ethyl]-1,2,3,5,10,10a-hexahydropyrrolidino[3,2-b]indol-4-ium 
• 208464-81-7 C₂₆H₂₈N₂O₂ 
• 209682-64-4 5-ethyl-3-{[1-methylpyrrolidin-2-yl]methyl}-1H-indole 
• 143577-60-0 (R)-5-(2-phenylsulphonylethenyl)-3-(N-methylpyrrolidine-2-yl-methyl)-1H-indole hydrobromide 
• 3112-85-4 methylphenylsulfonate 
• 143322-55-8 (R)-3-(1-methyl-2-pyrrolidinylmethyl)-1H-indole 
• 208464-46-4 (R)-5-bromo-3-[(N-methylpyrrolidin-2-yl)methyl]-1-benzoylindole 

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.

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.

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.