1,6-Naphthyridin-2(1H)-one, 1-(2,6-dichlorophenyl)-5-(2,4-difluorophenyl)-, 6-oxide

Base Information

• Chemical Name: 1,6-Naphthyridin-2(1H)-one, 1-(2,6-dichlorophenyl)-5-(2,4-difluorophenyl)-, 6-oxide
• CAS No.: 913556-82-8
• Molecular Formula: C20H10Cl2F2N2O2
• Molecular Weight: 419.214
• Mol file: 913556-82-8.mol

Synonyms:

Chemical Property of 1,6-Naphthyridin-2(1H)-one, 1-(2,6-dichlorophenyl)-5-(2,4-difluorophenyl)-, 6-oxide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1,6-Naphthyridin-2(1H)-one, 1-(2,6-dichlorophenyl)-5-(2,4-difluorophenyl)-, 6-oxide

There total 6 articles about 1,6-Naphthyridin-2(1H)-one, 1-(2,6-dichlorophenyl)-5-(2,4-difluorophenyl)-, 6-oxide which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 88.0%

1-(2,6-dichlorophenyl)-5-(2,4-difluorophenyl)-1,6-naphthyridin-2(1H)-one (444665-44-5) → 1-(2,6-dichlorophenyl)-5-(2,4-difluorophenyl)-1,6-naphthyridin-2(1H)-one 6-oxide (913556-82-8)

Guidance literature:

With 3-chloro-benzenecarboperoxoic acid; In toluene; at 20 ℃; for 24h;

DOI:10.1021/jo061618f

Reference yield:

4-bromo-2-chloro-3-iodo-pyridine (916203-52-6) → 1-(2,6-dichlorophenyl)-5-(2,4-difluorophenyl)-1,6-naphthyridin-2(1H)-one 6-oxide (913556-82-8)

Guidance literature:

Multi-step reaction with 3 steps

1: 80 percent / sodium acetate; potassium bromide / palladium(II) acetate / various solvent(s) / 90 - 100 °C

2: 91 percent / tetrabutylammonium bromide; triphenylphosphine; sodium carbonate / palladium(II) acetate; potassium chloride / toluene; H₂O / Heating

3: 88 percent / 3-chloroperoxybenzoic acid / toluene / 24 h / 20 °C

With tetrabutylammomium bromide; sodium acetate; sodium carbonate; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; potassium bromide; potassium chloride; palladium diacetate; In water; toluene; 1: Heck coupling / 2: Suzuki-Miyaura coupling;

DOI:10.1021/jo061618f

Reference yield:

5-chloro-1-(2,6-dichlorophenyl)-1,6-naphthyridin-2(1H)-one (916203-59-3) → 1-(2,6-dichlorophenyl)-5-(2,4-difluorophenyl)-1,6-naphthyridin-2(1H)-one 6-oxide (913556-82-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 91 percent / tetrabutylammonium bromide; triphenylphosphine; sodium carbonate / palladium(II) acetate; potassium chloride / toluene; H₂O / Heating

2: 88 percent / 3-chloroperoxybenzoic acid / toluene / 24 h / 20 °C

With tetrabutylammomium bromide; sodium carbonate; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; potassium chloride; palladium diacetate; In water; toluene; 1: Suzuki-Miyaura coupling;

DOI:10.1021/jo061618f

upstream raw materials:

1-(2,6-dichlorophenyl)-5-(2,4-difluorophenyl)-1,6-naphthyridin-2(1H)-one

4-bromo-2-chloro-3-iodo-pyridine

5-chloro-1-(2,6-dichlorophenyl)-1,6-naphthyridin-2(1H)-one

2-chloro-4-bromopyridine

Downstream raw materials:

7-chloro-1-(2,6-dichlorophenyl)-5-(2,4-difluorophenyl)-1,6-naphthyridin-2-(1H)-one

Refernces

• 1、 Chung, John Y. L.,Cvetovich, Raymond J.,McLaughlin, Mark,Amato, Joseph,Tsay, Fuh-Rong,Jensen, Mark,Weissman, Steve,Zewge, Daniel. "Synthesis of a naphthyridone p38 MAP kinase inhibitor". . p. 8602 - 8609. Retrieved 2007/10/03.