A convenient synthesis of the key intermediate of selective COX-2 inhibitor Etoricoxib
An original strategy for the synthesis of ketone 1, the key intermediate for preparing Etoricoxib, an important nonsteroidal anti-inflammatory drug, has been developed. Inexpensive 5-hydroxy-2-methylpyridine was converted to the corresponding acetyl derivative in four practical synthetic steps. The following palladium-catalyzed α-arylation of acetylpicoline with 4-bromo- or 4-chlorophenyl methyl sulfone was efficiently optimized in order to afford ketone 1 in remarkable yield.
1,2-Diaryl(3-pyridyl)ethanone oximes. Intermolecular hydrogen bonding networks revealed by X-ray diffraction
The synthesis of a set of 1-aryl-2-aryl(3-pyridyl)ethanones 1-5 and the corresponding ketoximes 6-9 is reported. Structural studies of oximes 6, 7 and 9 were performed in solution using 1H-NMR and in the solid state by X-ray crystallography, providing evidence of H-bonding networks. The crystal packing was controlled by homomeric intermolecular oxime...oxime H-bond interactions for 6 and cooperative oxime...N(pyridyl) and CH/π interactions for 7 and 9.
Alcalde, Ermitas,Mesquida, Neus,Alvarez-Rua, Carmen,Cuberes, Rosa,Frigola, Jordi,Garcia-Granda, Santiago
p. 301 - 318
(2008/09/16)
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