180637-89-2

Basic information

• Product Name: 3-[((2R)-1-METHYLPYRROLIDIN-2-YL)METHYL]-5-[(E)-2-(PHENYLSULFONYL)VINYL]INDOLE
• Synonyms: 3-[((2R)-1-METHYLPYRROLIDIN-2-YL)METHYL]-5-[(E)-2-(PHENYLSULFONYL)VINYL]INDOLE;(R)-3-[(1-Methyl-2-pyrrolidinyl)methyl]-5-[2-(phenylsulfonyl)ethenyl]-1H-indole;3-[[(2R)-1-Methyl-2-pyrrolidinyl]Methyl]-5-[2-(phenylsulfonyl)ethenyl]-1H-indole;(R)-3-((1-Methylpyrrolidin-2-yl)methyl)-5-(2-(phenylsulfonyl)vinyl)-1H-indole;(R)-5-[(2-phenylsulfonyl)ethenyl]-3-(N-methylpyrrolidine-2-ylmethyl)-1H-indole
• CAS NO: 180637-89-2
• Molecular Formula: C₂₂H₂₄N₂O₂S
• Molecular Weight: 380.5
• Product Categories: Chiral Reagents;Indole Derivatives;Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 180637-89-2.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 617.7°C at 760 mmHg
• Flash Point: 327.4°C
• Appearance: /
• Density: 1.263
• Vapor Pressure: 3.46E-15mmHg at 25°C
• Refractive Index: 1.655
• PKA: 16.92±0.30(Predicted)
• CAS DataBase Reference: 3-[((2R)-1-METHYLPYRROLIDIN-2-YL)METHYL]-5-[(E)-2-(PHENYLSULFONYL)VINYL]INDOLE(CAS DataBase Reference)
• NIST Chemistry Reference: 3-[((2R)-1-METHYLPYRROLIDIN-2-YL)METHYL]-5-[(E)-2-(PHENYLSULFONYL)VINYL]INDOLE(180637-89-2)
• EPA Substance Registry System: 3-[((2R)-1-METHYLPYRROLIDIN-2-YL)METHYL]-5-[(E)-2-(PHENYLSULFONYL)VINYL]INDOLE(180637-89-2)

Safety Data

• Hazardous Substances Data: 180637-89-2(Hazardous Substances Data)

Usage

Chemical Properties

Red Solid

InChI:InChI=1/C22H24N2O2S/c1-24-12-5-6-19(24)15-18-16-23-22-10-9-17(14-21(18)22)11-13-27(25,26)20-7-3-2-4-8-20/h2-4,7-11,13-14,16,19,23H,5-6,12,15H2,1H3/b13-11+/t19-/m1/s1

Upstream product

• 180637-88-1 (R)-1-acetyl-5-[2-(phenylsulfonyl)ethyenyl]-3-(N-methylpyrrolidin-2-ylmethyl)-1H-indole 
• 5535-48-8 PVS 
• 143322-57-0 (R)-5-bromo-3-(N-methylpyrrolidine-2-ylmethyl)-1H-indole 
• 205369-12-6 (R)-1-acetyl-5-bromo-3-(N-methylpyrrolidin-2-ylmethyl)-1H-indole 
• 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 

Downstream Products

• 143322-58-1 eletriptan 
• 1162655-06-2 3-[[(R)-1-methyl-2-pyrrolidinyl]methyl]-5-[2-(phenyl-sulfonyl)ethyl]indole para-toluenesulfonate 
• 1196663-26-9 (R)-5-(2-phenylsulphonylethenyl)-3-(N-methylpyrrolidin-2-ylmethyl)-1H-indole trifluoroacetate 
• 1196663-27-0 (R)-5-(2-phenylsulphonylethenyl)-3-(N-methylpyrrolidine-2-yl-methyl)-1H-indole formate 
• 1196663-24-7 (R)-5-(2-phenylsulphonylethenyl)-3-(N-methylpyrrolidine-2-yl-methyl)-1H-indole methanesulphonate 
• 1196663-25-8 (R)-5-(2-phenylsulphonylethenyl)-3-(N-methylpyrrolidin-2-ylmethyl)-1H-indole benzenesulfonate 
• 177834-92-3 eletriptan hydrobromide 
• 209682-64-4 5-ethyl-3-{[1-methylpyrrolidin-2-yl]methyl}-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 
• 1217641-89-8 (R)-5-[2-(phenylsulfonyl)ethyl]-3-[(1-methyl-2-pyrrolidinyl-N-oxide)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.

Process

The present invention provides an improved process for the preparation of α-polymorphic eletriptan hydrobromide.