724788-70-9

Basic information

• Product Name: 8-BROMO-7-FLUORO-2-METHOXY-1,5-NAPHTHYRIDINE
• Synonyms: 8-BROMO-7-FLUORO-2-METHOXY-1,5-NAPHTHYRIDINE;1,5-Naphthyridine,8-broMo-7-fluoro-2-Methoxy-;4-BroMo-3-fluoro-6-Methoxy-[1,5]naphthyridine
• CAS NO: 724788-70-9
• Molecular Formula: C₉H₆BrFN₂O
• Molecular Weight: 257.0591432
• Mol File: 724788-70-9.mol
• Article Data: 24

Chemical Properties

• Boiling Point: 324.699°C at 760 mmHg
• Flash Point: 150.173°C
• Appearance: /
• Density: 1.665g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.626
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 8-BROMO-7-FLUORO-2-METHOXY-1,5-NAPHTHYRIDINE(CAS DataBase Reference)
• NIST Chemistry Reference: 8-BROMO-7-FLUORO-2-METHOXY-1,5-NAPHTHYRIDINE(724788-70-9)
• EPA Substance Registry System: 8-BROMO-7-FLUORO-2-METHOXY-1,5-NAPHTHYRIDINE(724788-70-9)

Safety Data

• Hazardous Substances Data: 724788-70-9(Hazardous Substances Data)

Usage

General Description

8-Bromo-7-fluoro-2-methoxy-1,5-naphthyridine is a chemical compound with a molecular formula of C12H7BrFN2O. It is a naphthyridine derivative that contains bromine, fluorine, and methoxy functional groups. 8-BROMO-7-FLUORO-2-METHOXY-1,5-NAPHTHYRIDINE is used in pharmaceutical research and development, particularly in the synthesis of potential drug candidates. Its structure and properties make it a valuable building block for the design and synthesis of new drug molecules with potential therapeutic applications. Its unique chemical structure and reactivity make it a useful tool in drug discovery and development efforts.

InChI:InChI=1/C9H6BrFN2O/c1-14-7-3-2-6-9(13-7)8(10)5(11)4-12-6/h2-4H,1H3

Upstream product

• 38533-61-8 2-chloro-6-methoxy-3-nitropyridine 
• 1075259-75-4 2-fluoro-1-(6-methoxy-3-nitropyridin-2-yl)ethanone 
• 1075259-74-3 2-(1-ethoxyethylene)-6-methoxy-3-nitropyridine 
• 25063-69-8 5-[[(6-methoxypyridin-3-yl)amino]methylidene]-2,2-dimethyl-1,3-dioxane-4,6-dione 
• 724788-68-5 C₉H₆BrN₄O⁽¹⁺⁾ 
• 53241-92-2 4-Hydroxy-6-methoxy-[1,5]naphthyridine-3-carboxylic Acid Ethyl Ester 
• 53241-90-0 diethyl {[(6-methoxypyridin-3-yl)amino]methylidene}propanedioate 
• 23443-25-6 6-methoxy-1,5-naphthyridin-4-ol 
• 1075259-77-6 3-fluoro-6-methoxy-1,5-naphthyridin-4-ol 
• 724788-63-0 ethyl 6-methoxy-4-oxo-1,4-dihydro-1,5-naphthyridine-3-carboxylate 
• 1417551-48-4 t-butyl 4-bromo-6-methoxy-1,5-naphthyridine-3-yl-carbamate 
• 724788-66-3 4-bromo-6-(methyloxy)-1,5-naphthyridin-3-amine 
• 724788-65-2 4-bromo-6-methoxy-1,5-naphthyridine-3-carboxylic acid 
• 724788-64-1 ethyl 4-bromo-6-methoxy-1,5-naphthyridine-3-carboxylate 

Downstream Products

• 1616409-89-2 t-butyl 1-(2-(3-fluoro-6-methoxy-1,5-naphthyridin-4-yl)-1-hydroxyethyl)-2-oxabicyclo[2.2.2]octan-4-ylcarbamate 
• 1616409-88-1 t-butyl 1-(2-(3-fluoro-6-methoxy-1,5-naphthyridin-4-yl)-1-hydroxyethyl)-2-oxabicyclo[2.2.2]octan-4-ylcarbamate 
• 1415415-01-8 7-fluoro-2-methoxy-8-methyl-1,5-naphthyridine 
• 1207621-43-9 (3-fluoro-6-methoxy-[1,5]naphthyridin-4-yl)-acetic acid ethyl ester 
• 1073495-66-5 C₁₈H₁₅FN₂O₅S 
• 943026-50-4 C₁₈H₁₅FN₂O₅S 
• 1173896-46-2 1-(2-(4-((3,4-dichlorobenzyl)amino)piperidin-1-yl)ethyl)-7-methoxy-1,5-naphthyridin-2(1H)-one 
• 959615-59-9 7-methoxy-1,5-naphthyridin-2(1H)-one 

Relevant articles and documents

1,3-Dioxane-Linked Bacterial Topoisomerase Inhibitors with Enhanced Antibacterial Activity and Reduced hERG Inhibition

The development of new therapies to treat methicillin-resistant Staphylococcus aureus (MRSA) is needed to counteract the significant threat that MRSA presents to human health. Novel inhibitors of DNA gyrase and topoisomerase IV (TopoIV) constitute one highly promising approach, but continued optimization is required to realize the full potential of this class of antibiotics. Herein, we report further studies on a series of dioxane-linked derivatives, demonstrating improved antistaphylococcal activity and reduced hERG inhibition. A subseries of analogues also possesses enhanced inhibition of the secondary target, TopoIV.

TYPE II TOPOISOMERASE INHIBITORS AND METHODS OF MAKING AND USING THEREOF

Disclosed are Type II Topoisomerase Inhibitors, analogs thereof, pharmaceutical compositions thereof, and methods of making and using these compounds and compositions. Methods of using the disclosed compounds to treat infections, such as MRSA, MDR P. aeruginosa, and other pathogens are also described.

A one-pot diazotation-fluorodediazoniation reaction and fluorine gas for the production of fluoronaphthyridines

Several synthetic routes to 7-fluoro-2-methoxy-8-methyl-1,5-naphthyridine (1) are presented, and their suitability for scale-up is discussed. The way of introducing the fluorine atom is crucial. Early routes start from commercially available fluorinated building blocks or employ F+ reagents like SelectFluor and delivered up to 70 kg of 7-fluoro-2-methoxy-1,5-naphthyridine (18). To prepare for larger scales, the focus turned to the use of HF or elemental fluorine, both one of the cheapest sources of fluorine. The first method, a one-pot diazotation-fluorodediazoniation with 6-methoxy-1,5- naphthyridin-3-amine (9) in HF gave the fluorinated naphthyridine 18 in high yield and purity without isolation of the unstable diazonium salt, the latter being a severe drawback of the related Balz-Schiemann protocol. The second method relies on the use of fluorine gas for a surprisingly selective ortho-fluorination of 6-methoxy-1,5-naphthyridin-4-ol (10).