新产品编号:941799
Chemical Name: 1-(3-Fluorophenyl)-1-[6-[4-(methylsulfonyl)phenyl]-1,3-benzodioxol-5-yl]methanone
CAS No. 445039-17-8
项目整合开发状态: Preclinical
项目研究机构: NitroMed (Originator)
合成路线:Piperonal (I) is brominated by means of Br2 in AcOH to produce (II).Subsequent Suzuki coupling of aryl bromide (II) with 4-(methylsulfanyl)benzeneboronic acid (III) furnishes adduct (IV).Addition of 3-fluorophenylmagnesium bromide (V) to aldehyde (IV) leads to carbinol (VI).The sulfide group is further oxidized to sulfone (VII) employing oxone in aqueous MeOH.Finally,oxidation of alcohol (VII) with pyridinium chlorochromate provides the target ketone.(1,2)
📌 参考资料/链接：
参考文献标题:Substd.aryl cpds.as novel cyclooxygenase-2 selective inhibitors,compsns.and methods of use
文献作者:Earl,R.A.; Garvey,D.S.; Khanapure,S.P.; Gaston,R.D.; Fang,X.; Ezawa,M.(NitroMed Inc.)
参考来源:US 2002119977; WO 0260378
📄 详细内容
合成路线:Piperonal (I) is brominated by means of Br2 in AcOH to produce (II).Subsequent Suzuki coupling of aryl bromide (II) with 4-(methylsulfanyl)benzeneboronic acid (III) furnishes adduct (IV).Addition of 3-fluorophenylmagnesium bromide (V) to aldehyde (IV) leads to carbinol (VI).The sulfide group is further oxidized to sulfone (VII) employing oxone in aqueous MeOH.Finally,oxidation of alcohol (VII) with pyridinium chlorochromate provides the target ketone.(1,2)
参考文献标题:Design and synthesis of novel benzo-dioxolane cyclooxygenase (COX-2) selective inhibitors
文献作者:Ezawa,M.; Khanapure,S.P.; Garvey,D.S.; Young,D.; Earl,R.; Gaston,R.; Fang,F.; Marek,P.; Shumway,M.; Trocha,M.; Tam,S.W.; Janero,D.R.; Letts,L.G.
参考来源:225th ACS Natl Meet (March 23 2003,New Orleans) 2003,Abst MEDI 243