654655-69-3

Basic information

• Product Name: 3-benzyl-6-bromo-2-methoxyquinoline
• Synonyms: 3-benzyl-6-bromo-2-methoxyquinoline;6-Bromo-2-methoxy-3-benzylquinoline;6-bromo-2-methoxy-3-(phenylmethyl)-Quinoline;Bedaquiline int-2 3-Benzyl-6-bromo-2-methoxyquinoline;Quinoline, 6-bromo-2-methoxy-3-(phenylmethyl)-;Bedaquiline Impurity A;3-BENZYL 1-6-BROMO-2-METHOXYQUINOLINE
• CAS NO: 654655-69-3
• Molecular Formula: C₁₇H₁₄BrNO
• Molecular Weight: 328
• EINECS: 207-791-3
• Product Categories: bedaquiline intermediates
• Mol File: 654655-69-3.mol
• Article Data: 18

Chemical Properties

• Melting Point: 82-83℃
• Boiling Point: --
• Flash Point: --
• Appearance: Off-White Solid
• Density: --
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• PKA: 2.45±0.50(Predicted)
• CAS DataBase Reference: 3-benzyl-6-bromo-2-methoxyquinoline(CAS DataBase Reference)
• NIST Chemistry Reference: 3-benzyl-6-bromo-2-methoxyquinoline(654655-69-3)
• EPA Substance Registry System: 3-benzyl-6-bromo-2-methoxyquinoline(654655-69-3)

Safety Data

• Hazardous Substances Data: 654655-69-3(Hazardous Substances Data)

Usage

Description

3-Benzyl-6-bromo-2-methoxyquinoline is an organic compound characterized by its white solid appearance. It is a quinoline derivative with a benzyl group at the 3rd position, a bromine atom at the 6th position, and a methoxy group at the 2nd position. 3-benzyl-6-bromo-2-methoxyquinoline is known for its potential applications in the pharmaceutical industry due to its unique chemical structure and properties.

Uses

Used in Pharmaceutical Industry:
3-Benzyl-6-bromo-2-methoxyquinoline is used as a reactant for the preparation of Bedaquiline (B119550), a potential drug in the treatment of tuberculosis. Its role in the synthesis of Bedaquiline highlights its importance in the development of novel therapeutic agents for combating drug-resistant tuberculosis.
As a chemical intermediate, 3-benzyl-6-bromo-2-methoxyquinoline may also have potential applications in the synthesis of other pharmaceutical compounds, given its unique structural features. However, further research and development are necessary to explore its full potential in various industries.

Upstream product

• 654655-68-2 3-benzyl-6-bromo-2-chloro-quinoline 
• 124-41-4 sodium methylate 
• 67-56-1 methanol 
• 106-40-1 4-bromo-aniline 
• 654655-80-8 1-(6-bromo-2-methoxyquinolin-3-yl)-4-(dimethylamino)-2-(naphthalen-1-yl)-1-phenylbutan-2-ol 
• 316146-27-7 N-(4-bromophenyl)-3-phenylpropanamide 
• 501-52-0 3-Phenylpropionic acid 
• 99455-05-7 2-methoxy-6-bromoquinoline 
• 100-39-0 benzyl bromide 
• 645-45-4 hydrocinnamic acid chloride 
• 105479-98-9 ethyl 2-(acetoxy(phenyl)methyl)acrylate 
• 37442-45-8 ethyl 2-(hydroxy(phenyl)methyl)propenoate 
• 924658-20-8 2-[(4-bromo-phenylamino)-phenyl-methyl]-acrylic acid ethyl ester 
• 924633-09-0 3-benzyl-6-bromo-1H-quinolin-2-one 

Downstream Products

• 654655-75-1 2-(N-methylbenzyl)aminoethyl-1-naphthylketone 
• 861709-20-8 C₃₈H₃₅BrN₂O₂ 
• 916800-41-4 C₃₅H₃₃BrF₂N₂O₂ 

Relevant articles and documents

PROCESS FOR THE PREPARATION OF BEDAQUILINE FUMARATE

The present disclosure relates to an improved process for the preparation of bedaquiline fumarate, comprising a step of preparing bedaquiline by reaction of 3-benzyl-6-bromo-2-methoxyquinoline 5 with 3-(dimethylamino)-l-(naphthalen-l-yl)propan-l-one 4 in the presence of lithium pyrrolidide.

A method of high-efficiency production of beda quinoline

The invention relates to a method for high efficiency production of Bedaquiline. The method comprises that through optical resolution of 1-(6-bromo-2-methoxy-3-quinolyl)-4-dimethylamino-2-(1-naphthyl)-1-phenyl-2-butanol, Bedaquiline and other isomers are obtained, the other isomers undergo a reaction under the action of an alkali to produce key intermediate compounds A and B, and the key intermediate compounds A and B are separated and undergo a reaction to produce Bedaquiline. The method realizes high efficiency production of Bedaquiline, prevents large waste of materials, saves a cost and is suitable for large scale industrial production.

Structural Simplification of Bedaquiline: the Discovery of 3-(4-(N,N-Dimethylaminomethyl)phenyl)quinoline-Derived Antitubercular Lead Compounds

Bedaquiline (BDQ) is a novel and highly potent last-line antituberculosis drug that was approved by the US FDA in 2013. Owing to its stereo-structural complexity, chemical synthesis and compound optimization are rather difficult and expensive. This study