143322-57-0

Usage

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 
• 105370-80-7 (R)-pyrrolidine-1,2-dicarboxylic acid 1-phenyl ester 
• 1353991-67-9 (R)-2-chlorocarbonylpyrrolidine-1-carboxylic acid phenyl ester 
• 1353991-68-0 (R)-2-(5-bromo-1H-indole-3-carbonyl)pyrrolidine-1-carboxylic acid 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 
• 208464-46-4 (R)-5-bromo-3-[(N-methylpyrrolidin-2-yl)methyl]-1-benzoylindole 
• 180637-89-2 (R)-5-[(2-phenylsulfonyl)ethenyl]-3-(N-methylpyrrolidine-2-ylmethyl)-1H-indole 
• 3112-85-4 methylphenylsulfonate 
• 177834-92-3 eletriptan hydrobromide 
• 205369-12-6 (R)-1-acetyl-5-bromo-3-(N-methylpyrrolidin-2-ylmethyl)-1H-indole 
• 143322-58-1 eletriptan 
• 143577-60-0 (R)-5-(2-phenylsulphonylethenyl)-3-(N-methylpyrrolidine-2-yl-methyl)-1H-indole hydrobromide 
• 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 
• 209682-64-4 5-ethyl-3-{[1-methylpyrrolidin-2-yl]methyl}-1H-indole 
• 208464-81-7 C₂₆H₂₈N₂O₂ 
• 143322-55-8 (R)-3-(1-methyl-2-pyrrolidinylmethyl)-1H-indole 

Relevant academic research and scientific papers

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.

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--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.

Salts of (R)-5-(2phenylsulphonylethenyl)-3-(N-methylpyrrolidin-2-ylmethyl)-1H-indole, 5-bromo-3-[(R)-1-methyl-pyrrolidin-2-ylmethyl]-1H-indole and of eletriptan

The present invention relates to salts of (R)-5-(2-phenylsulphonylethenyl)-3-(N-methylpyrrolidin-2-ylmethyl)-1H-indole of the formula: wherein HX is an acid selected from para-toluene sulfonic acid, benzene sulphonic acid, trifluoroacetic acid, methane sulphonic acid, formic acid and succinic acid; and to processes of preparing and using such salts.

Process for preparing 5-bromo-3-[(R)-1-methyl-pyrrolidin-2-ylmethyl]-1H-indole

The invention encompasses a process for preparing 5-bromo-3-[(R)-1-methyl-pyrrolidin-2-ylmethyl]-1H-indole comprising reacting (R)-2-(5-bromo-1H-indole-3-carbonyl)-pyrrolidine-1-carboxylic acid benzyl ester with a reducing agent selected from the group consisting of sodium dihydro-bis(2-methoxyethoxy)aluminate, lithium tris[(3-ethyl-3-pentyl)oxy]aluminohydride, lithium tri-tert-butoxyaluminum hydride and diisobutylaluminium hydride. 5-bromo-3-[(R)-1-methyl-pyrrolidin-2-ylmethyl]-1H-indole is a key intermediate for preparing eletriptan and its salts thereof.

5-CYCLO INDOLE COMPOUNDS AS 5-HT1D RECEPTOR LIGANDS

Described herein are compounds selective for a 5-HT1D-like receptor, which have general formula (I), wherein A is selected from a six-membered, non-aromatic, optionally substituted carbocycle and a six-membered, non-aromatic, optionally substituted heterocycle having one or two heteroatoms selected from O, S, SO, SO2 and NR; R is selected from H and OH; n is 0 or 1 as permitted by chemical structure; R is selected from CRRCH2NRR or a group of formula (II), (III) or (IV); R is selected from H and benzoyl; R is selected from H, loweralkyl, benzyl, loweralkylcarbonyl, loweralkylaminocarbonyl; loweralkylaminothiocarbonyl, loweralkanoyl, loweralkylaminoimide and loweralkoxy-substituted loweralkylene; R and R are independently selected from H, loweralkoxy and hydroxy; R and R are independently selected from H and loweralkyl or R and R form an alkylene bridge which, together with the nitrogen atom to which they are attached, creates an optionally substituted 3- to 6-membered ring; ----- denotes a single or double bond; and R, R and R are independently selected from H and loweralkyl. Also described is the use of these compounds as pharmaceuticals to treat indications where stimulation of a 5-HT1D-like receptor is implicated, such as migraine.

(R)-3-(N-Methylpyrrolidin-2-ylmethyl)-5-(1,2,3,6-tetrahydropyridin-4-yl) -1H-indole derivatives as high affinity h5-HT1B/1D ligands

A series of (R)-3-(N-methylpyrrolidin-2-ylmethyl)-5-(1,2,3,6-tetrahydropyridin-4-yl) -1H-indole derivatives (2) have been prepared using parallel synthesis, and their structure-activity relationship studied. High affinity human 5-HT 1B/1D (h5-HT1B/1D) ligands have been identified.

Pyrrolidine-indole compounds having 5-HT6 affinity

Described herein are compounds with affinity for the 5-HT 6 receptor, which have the general formula: STR1 wherein: R 1 is selected from the group consisting of H and C 1-4 alkyl;R 2 is selected from the group consisting of H, C 1-4 alkyl and benzyl;R 3 is selected from the group consisting of COR 5, SO 2 R 5, CONHC 1-4 alkyl and C(S)SR 6 ;R 4a is selected from the group consisting of H, OH, halo, C 1-4 alkyl and C 1-4 alkoxy;R 4b is selected from the group consisting of H, hydroxy, halo, C 3-7 cycloalkyloxy, C 1-4 alkoxy, C 1-4 alkyl, benzyloxy, phenoxy, trifluoromethyl, trifluoromethoxy and vinyl;R 4c is selected from the group consisting of H, OH, halo, C 1-4 alkyl and C 1-4 alkoxy;R 4d is selected from the group consisting of H, OH, halo, C 1-4 alkyl and C 1-4 alkoxy;R 5 is selected from the group consisting of phenyl, pyridyl, thienyl, quinolinyl and naphthyl which are optionally substituted with 1-4 substituents selected from C 1-4 alkoxy, C 1-4 alkyl, halo, nitro, trifluoromethyl, trifluoromethoxy, 1,2-methylenedioxy, C 1-4 alkylcarbonyl, C 1-4 alkoxycarbonyl and C 1-4 alkylS--; andR 6 is selected from C 1-4 alkyl, allyl, propargyl and optionally substituted benzyl wherein the benzyl group is optionally substituted with 1-4 substituents selected from cyano, C 1-4 alkyl and halo.Also described is the use of these compounds as pharmaceuticals to treat indications where inhibition of the 5-HT 6 receptor is implicated, such as schizophrenia.