5-Chloro-6'-Methyl-3-[4-(Methylsulfonyl)phenyl]-2,3'-bipyridine 1'-Oxide

Base Information

• Chemical Name: 5-Chloro-6'-Methyl-3-[4-(Methylsulfonyl)phenyl]-2,3'-bipyridine 1'-Oxide
• CAS No.: 325855-74-1
• Molecular Formula: C18H15ClN2O3S
• Molecular Weight: 374.84100
• Mol file: 325855-74-1.mol

Synonyms:Etoricoxib N1'-Oxide;Etoricoxib-1'-N-Oxide;

Chemical Property of 5-Chloro-6'-Methyl-3-[4-(Methylsulfonyl)phenyl]-2,3'-bipyridine 1'-Oxide

Chemical Property:

• Melting Point: 204-206°C
• Boiling Point: 603.5±55.0 °C(Predicted)
• PKA: 0.25±0.10(Predicted)
• PSA: 80.87000
• Density: 1.35±0.1 g/cm3(Predicted)
• LogP: 5.29020
• Storage Temp.: Sealed in dry,Store in freezer, under -20°C
• Solubility.: Chloroform (Slightly), DMSO (Slightly, Sonicated), Methanol (Slightly, Heated)

Purity/Quality:

HPLC≥98% ^*data from raw suppliers

EtoricoxibN1’-Oxide ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: Etoricoxib N1’Oxide is an impurity of Etoricoxib (E934100). Etoricoxib N1’-Oxide is an impurity of Etoricoxib (E934100).

Technology Process of 5-Chloro-6'-Methyl-3-[4-(Methylsulfonyl)phenyl]-2,3'-bipyridine 1'-Oxide

There total 3 articles about 5-Chloro-6'-Methyl-3-[4-(Methylsulfonyl)phenyl]-2,3'-bipyridine 1'-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: 89.0%

Etoricoxib → Etoricoxib-1'-N-Oxide (325855-74-1)

Guidance literature:

With 3-chloro-benzenecarboperoxoic acid;

DOI:10.1021/ol006831r

Reference yield: 62.0%

etoricoxib (202409-33-4) → Etoricoxib-1'-N-Oxide (325855-74-1)

Guidance literature:

With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at 20 ℃; for 0.5h;

DOI:10.1016/S0960-894X(01)00135-4

Reference yield:

1-(6-methyl-3-pyridinyl)-2-[4-(methylsulfonyl)phenyl]ethanone (221615-75-4) → Etoricoxib-1'-N-Oxide (325855-74-1)

Guidance literature:

Multi-step reaction with 2 steps

1.1: t-BuOK / tetrahydrofuran / 0.75 h / 20 °C

1.2: 85 percent / AcOH; TFA; NH₂OH*HCl / tetrahydrofuran; H₂O / 5 h / Heating

2.1: 89 percent / mCPBA

With potassium tert-butylate; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran;

DOI:10.1021/ol006831r

upstream raw materials:

etoricoxib

1-(6-methyl-3-pyridinyl)-2-[4-(methylsulfonyl)phenyl]ethanone

Downstream raw materials:

6'-Hydroxymethyletoricoxib

Refernces

• 1、 Chauret, Nathalie,Yergey, James A,Brideau, Christine,Friesen, Richard W,Mancini, Joseph,Riendeau, Denis,Silva, Jose,Styhler, Angela,Trimble, Laird A,Nicoll-Griffith, Deborah A. "In vitro metabolism considerations, including activity testing of metabolites, in the discovery and selection of the COX-2 inhibitor etoricoxib (MK-0663)". . p. 1059 - 1062. Retrieved 2007/10/03.