1003944-32-8

Basic information

• Product Name: 7-Fluoro-2-(methyloxy)-1,5-naphthyridine
• Synonyms: 7-Fluoro-2-(methyloxy)-1,5-naphthyridine;7-Fluoro-2-methoxy-1,5-naphthyridine
• CAS NO: 1003944-32-8
• Molecular Weight: 178.166
• Mol File: 1003944-32-8.mol
• Article Data: 8

Chemical Properties

• Melting Point: 78-79℃
• CAS DataBase Reference: 7-Fluoro-2-(methyloxy)-1,5-naphthyridine(CAS DataBase Reference)
• NIST Chemistry Reference: 7-Fluoro-2-(methyloxy)-1,5-naphthyridine(1003944-32-8)
• EPA Substance Registry System: 7-Fluoro-2-(methyloxy)-1,5-naphthyridine(1003944-32-8)

Safety Data

• Hazardous Substances Data: 1003944-32-8(Hazardous Substances Data)

Upstream product

• 1075259-77-6 3-fluoro-6-methoxy-1,5-naphthyridin-4-ol 
• 1075259-75-4 2-fluoro-1-(6-methoxy-3-nitropyridin-2-yl)ethanone 
• 1075259-74-3 2-(1-ethoxyethylene)-6-methoxy-3-nitropyridine 
• 38533-61-8 2-chloro-6-methoxy-3-nitropyridine 
• 67-56-1 methanol 
• 1378470-92-8 C₈H₄ClFN₂ 
• 124-41-4 sodium methylate 
• 959615-64-6 7-fluoro-1,5-naphthyridin-2(1H)-one 
• 38186-88-8 2-chloro-5-fluoronicotinic acid 
• 82671-06-5 2,6-dichloro-5-fluoro-3-pyridinecarboxylic acid 
• 1449421-73-1 6-methoxy-3-nitro-1,5-naphthyridin-4-ol 
• 25063-69-8 5-[[(6-methoxypyridin-3-yl)amino]methylidene]-2,2-dimethyl-1,3-dioxane-4,6-dione 
• 6628-77-9 6-methoxy-pyridin-3-ylamine 
• 23443-25-6 6-methoxy-1,5-naphthyridin-4-ol 

Downstream Products

• 1415415-01-8 7-fluoro-2-methoxy-8-methyl-1,5-naphthyridine 
• 959615-59-9 7-methoxy-1,5-naphthyridin-2(1H)-one 

Relevant articles and documents

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).

Process for Manufacturing a Naphthyridine Derivative

The invention relates to a process and synthetic intermediates that can be used for manufacturing the compound of formula (1-6) which is a synthetic intermediate useful in the preparation of antibiotic compounds.

NAPHTHYRIDIN-2 (1 H)-ONE COMPOUNDS USEFUL AS ANTIBACTERIALS

Compounds of Formula (I) wherein substituents R1, R2 and R5 are as defined, and Ar represents substituted phenyl, pyridyl, pyridazinyl, pyrimidinyl, pyrazinyl, thiazolyl, furanyl, imidazolyl and thiophenyl substituted by a hydroxyalkyl substituent and an optional other substituent; compositions containing them, their use in therapy, including their use as antibacterials, for example in the treatment of tuberculosis, and methods for the preparation of such compounds, are provided.