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

• 501-52-0 3-Phenylpropionic acid 
• 654655-80-8 1-(6-bromo-2-methoxyquinolin-3-yl)-4-(dimethylamino)-2-(naphthalen-1-yl)-1-phenylbutan-2-ol 
• 99455-05-7 2-methoxy-6-bromoquinoline 
• 100-39-0 benzyl bromide 
• 645-45-4 hydrocinnamic acid chloride 
• 316146-27-7 N-(4-bromophenyl)-3-phenylpropanamide 
• 106-40-1 4-bromo-aniline 
• 654655-68-2 3-benzyl-6-bromo-2-chloro-quinoline 
• 67-56-1 methanol 
• 124-41-4 sodium methylate 
• 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.

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

6-Cyano Analogues of Bedaquiline as Less Lipophilic and Potentially Safer Diarylquinolines for Tuberculosis

Bedaquiline (1) is a new drug for tuberculosis and the first of the diarylquinoline class. It demonstrates excellent efficacy against TB but induces phospholipidosis at high doses, has a long terminal elimination half-life (due to its high lipophilicity), and exhibits potent hERG channel inhibition, resulting in clinical QTc interval prolongation. A number of structural ring A analogues of bedaquiline have been prepared and evaluated for their anti-M.tb activity (MIC90), with a view to their possible application as less lipophilic second generation compounds. It was previously observed that a range of 6-substituted analogues of 1 demonstrated a positive correlation between potency (MIC90) toward M.tb and drug lipophilicity. Contrary to this trend, we discovered, by virtue of a clogP/M.tb score, that a 6-cyano (CN) substituent provides a substantial reduction in lipophilicity with only modest effects on MIC values, suggesting this substituent as a useful tool in the search for effective and safer analogues of 1.