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

Chemical Properties

Light Brown Solid

Uses

5-Bromo Eletriptan is an impurity of Eletriptan (E505000), which is A serotonin 5-HTIB/ID receptor agonist, used for the treatment of migraine headaches.

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

• 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 
• 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 

Downstream Products

• 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 
• 177834-92-3 eletriptan hydrobromide 
• 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 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 PREPARATION OF ELETRIPTAN AND SALT THEREOF

The present invention relates to an improved process for the preparation of 3-(N-methyl-2(R)-pyrrolidinyl methyl)-5-[2-(phenyl sulfonyl)ethyl]-1H-indole or pharmaceutically acceptable salts thereof, particularly 3-(N-methyl-2(R)-pyrrolidinyl methyl)-5-[2-(phenyl sulfonyl)ethyl]-1H-indole hydrobromide (Eletriptan hydrobromide). The present invention further relates to novel polymorphs of 3-(N-methyl-2(R)-pyrrolidinyl methyl)-5-[2-(phenyl sulfonyl)ethenyl]-1H-indole hydrobromide and process for preparation thereof.

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.