331842-86-5

Basic information

• Product Name: benzyl 2-(5-broMo-1H-indole-3-carbonyl)pyrrolidine-1-carboxylate
• Synonyms: benzyl 2-(5-broMo-1H-indole-3-carbonyl)pyrrolidine-1-carboxylate
• CAS NO: 331842-86-5
• Molecular Formula: C21H19BrN2O3
• Molecular Weight: 427.29116
• EINECS: 921-090-6
• Mol File: 331842-86-5.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: benzyl 2-(5-broMo-1H-indole-3-carbonyl)pyrrolidine-1-carboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: benzyl 2-(5-broMo-1H-indole-3-carbonyl)pyrrolidine-1-carboxylate(331842-86-5)
• EPA Substance Registry System: benzyl 2-(5-broMo-1H-indole-3-carbonyl)pyrrolidine-1-carboxylate(331842-86-5)

Safety Data

• Hazardous Substances Data: 331842-86-5(Hazardous Substances Data)

Upstream product

• 10075-50-0 5-bromo-1H-indole 
• 79-37-8 oxalyl dichloride 
• 925-90-6 ethylmagnesium bromide 
• 61350-62-7 N-benzyloxycarbonyl-D-proline acid chloride 
• 6404-31-5 Z-D-proline 
• 676-58-4 methylmagnesium chloride 
• 61350-60-5 (S)-benzyloxycarbonyl-proline acid chloride 
• 144-55-8 sodium hydrogencarbonate 

Downstream Products

• 208464-46-4 (R)-5-bromo-3-[(N-methylpyrrolidin-2-yl)methyl]-1-benzoylindole 
• 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 
• 208464-45-3 (S)-5-bromo-3-[(N-methylpyrrolidin-2-yl)methyl]-1-benzoylindole 
• 208464-81-7 C₂₆H₂₈N₂O₂ 

Relevant articles and documents

A preparation method of the midbody according to sets up Qu Tan

The invention discloses a preparation method for an eletriptan intermediate. The preparation method comprises the following steps: in an organic solvent, and under the catalytic action of a Lewis acid, 5-bromoindole and N-benzyloxycarbonyl prolyl chloride

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.

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.

Conformationally constrained 5-(thienyl)tryptamine derivatives as serotonin 5-HT(1B/1D) receptor agonists: Potential treatments for migraine

In the search for human 5-HT(1D) selective agonists, a series of conformationally constrained 5-(2- or 3-thienyl)tryptamine derivatives 7, 10, and 12 have been synthesized. In vitro binding experiments at the cloned human 5-HT(1D) and 5-HT(1B) receptors h

5-ALKENYL AND 5-ALKYNYL INDOLE COMPOUNDS

Described herein are compounds selective for 5-HT 1D-like receptors, which have the general formula: STR1 wherein: R 1 is selected from H, aryl and aryl substituted with 1, 2 or 3 substituents independently selected from loweralkyl, loweralkoxy, loweralkylcarbonyl, loweralkyl-S--, loweralkyl-S(O)--, loweralkyl-SO 2-, S=C=N--, O=C=N--, halo, loweralkoxycarbonyl, nitro, amino, loweralkyl-NH--, (loweralkyl) 2--N--, loweralkyl-SO 2-loweralkyl-; A is a double or triple bond;R 2 is selected from a group of Formula II, III, IV and V: STR2 R 3 is selected from H and loweralkyl; R 4 is selected from H and loweralkyl; One of R 5 and R 6 is H and the other is independently selected from H, loweralkoxy, loweralkyl and hydroxy; andR 7 and R 8 are independently selected from H and loweralkyl or R 7 and R 8, together with the nitrogen atom to which they are attached, form an optionally substituted 3-to 6-membered ring;or a salt, solvate or hydrate thereof.Also described is the use of these compounds as pharmaceuticals to treat indications where stimulation of the 5-HT 1D-like receptor is implicated, such as migraine.