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

• 724788-70-9 8-bromo-7-fluoro-2-methoxy-1,5-naphthyridine 
• 67-56-1 methanol 
• 1378470-92-8 C₈H₄ClFN₂ 
• 1236221-93-4 6-(methyloxy)-1,5-naphthyridin-3-amine 
• 23443-25-6 6-methoxy-1,5-naphthyridin-4-ol 
• 6628-77-9 6-methoxy-pyridin-3-ylamine 
• 25063-69-8 5-[[(6-methoxypyridin-3-yl)amino]methylidene]-2,2-dimethyl-1,3-dioxane-4,6-dione 
• 1449421-73-1 6-methoxy-3-nitro-1,5-naphthyridin-4-ol 
• 82671-06-5 2,6-dichloro-5-fluoro-3-pyridinecarboxylic acid 
• 38186-88-8 2-chloro-5-fluoronicotinic acid 
• 959615-64-6 7-fluoro-1,5-naphthyridin-2(1H)-one 
• 124-41-4 sodium methylate 
• 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 

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.

Target-directed synthesis of antibacterial drug candidate GSK966587

(Equation Presented). An efficient enantioselective total synthesis of the potent antibiotic GSK966587 was accomplished. Highlights of the synthesis include two innovative Heck reactions, a highly selective zincate base directed ortho-metalation, Sharpless asymmetric epoxidation, and a fully convergent final step fragment coupling.