1-(6-Methylpyridin-3-yl)-2-(4-(methylsulfonyl)phenyl)ethanone Chemical Properties

Melting point:

>169oC (dec.)

Boiling point:

509.7±50.0 °C(Predicted)

Density 

1.242±0.06 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

solubility 

DMSO (Slightly), Methanol (Slightly, Heated)

pka

3.75±0.10(Predicted)

form 

Solid

color 

Pale Beige

InChI

InChI=1S/C15H15NO3S/c1-11-3-6-13(10-16-11)15(17)9-12-4-7-14(8-5-12)20(2,18)19/h3-8,10H,9H2,1-2H3

InChIKey

YBFHILNBYXCJKD-UHFFFAOYSA-N

SMILES

C(=O)(C1=CC=C(C)N=C1)CC1=CC=C(S(C)(=O)=O)C=C1

1-(6-Methylpyridin-3-yl)-2-(4-(methylsulfonyl)phenyl)ethanone Usage And Synthesis

Uses

This compound is an impurity in the synthesis of Etoricoxib (E934100), a specific inhibitor of COX-2 .

Synthesis

General procedure for the synthesis of 2-(4-methylsulfonylphenyl)-1-(6-methylpyridin-3-yl)-ethanone from 1-(6-methylpyridin-3-yl)-2-(4-(methylsulfanyl)phenyl)ethanone: 100 g of 1-(6-methylpyridin-3-yl)-2-[4-(methylsulfanyl)phenyl]ethanone (1.0 equiv.), 150 mL of ice-cold acetic acid (1.5 volume) and 30 mL of methanesulfonic acid (1.2 eq., 0.3 v/v; molecular weight 96.11 g/mol, density 1.481 g/mL) were added to a 3,000 mL three-necked flask fitted with a pyrometer, condenser, and dropping funnel. The reaction mixture was cooled to 5-10 °C. Under stirring, 120 mL of 30% w/w hydrogen peroxide solution (3 equiv, 1.20 v/v; molecular weight 34.02 g/mol, density 1.13 g/mL) was added slowly and dropwise at 5-10°C. The reaction mixture was warmed to 50 °C with stirring at 20-25 °C and kept reacting for at least 6 hours. Upon completion of the reaction, the mixture was cooled to 0-5 °C and a solution comprising 300 g of sodium thiosulfate (3 wt.) and water (10 v/v) was added in batches to a total volume of about 180-260 mL. The pH of the reaction mixture was adjusted with a 30% sodium hydroxide solution to 5.5-6.5. The mixture was continued to be stirred at 20-25 °C for 2 h. The suspension was then filtered. The solid product was washed with 2 x 400 mL of water and subsequently dried under vacuum at 40 °C for at least 12 hours. A final product of 105.7 g of the target product was obtained, which was analyzed by HPLC with a purity of 94% and a molar yield of 97.5% (area percentage).

References

[1] Patent: US2012/232281, 2012, A1. Location in patent: Page/Page column 7
[2] Journal of Organic Chemistry, 2000, vol. 65, # 25, p. 8415 - 8420
[3] Patent: US6369275, 2002, B1. Location in patent: Page column 17
[4] Patent: CN104045596, 2017, B. Location in patent: Paragraph 0056-0057
[5] Patent: CN108689917, 2018, A. Location in patent: Paragraph 0036; 0044; 0051-0054; 0062-0065

1-(6-Methylpyridin-3-yl)-2-(4-(methylsulfonyl)phenyl)ethanone(221615-75-4)Related Product Information

• Etoricoxib Impurity 11
• Etoricoxib Impurity 12
• lithiuM 2-(4-(Methylsulfonyl)phenyl)acetate
• 3 aMino-2-chloroacrolein
• (E)-2-chloro-3-iMino-N,N-diMethylprop-1-en-1-aMine hydrochloride
• (Z)-1-(6-methylpyridin-3-yl)-2-(4-(methylsulfonyl)phenyl)ethanone oxime
• Etoricoxib
• 2-Methylindole
• Etoricoxib Impurity 7
• 6'-DesMethyl-6'-carboxy Etoricoxib
• 2-CHLORO-1,3-DIMETHYLAMINO TRIMETHINIUM HEXAFLUOROPHOSPHATE
• Etoricoxib Impurity 18
• 5-Chloro-6'-Methyl-3-[4-(Methylsulfonyl)phenyl]-2,3'-bipyridine 1'-Oxide
• Etoricoxib impurity 22
• Etoricoxib IMpurity
• Etoricoxib Impurity 15
• Etoricoxib Impurity 19
• Deschloro Etoricoxib