新产品编号:1468605
Chemical Name: 2-[5-[3-Cyclopentyloxy-4-methoxyphenyl]furan-2-yl]pyridine
项目整合开发状态: Preclinical
项目研究机构: Merck Frosst (Originator)
合成路线:The Grignard reaction of 3-(cyclopentyloxy)-4-methoxybenzaldehyde (I) with vinylmagnesium bromide in THF gives the vinyl carbinol (II),which is oxidized with MnO2 in ethyl acetate yielding the propenone (III).The condensation of (III) with pyridine-2-carbaldehyde (IV) by means of 3-ethyl-5-(2-hydroxyethyl)-4-methyl-thiazolium bromide (ETB) and triethylamine affords the butanedione (V),which is finally cyclized to the target compound with p-toluenesulfonic acid in refluxing toluene.
📌 参考资料/链接：
参考文献标题:Aryl furan derivs.as PDE IV inhibitors
文献作者:Young,R.N.; MacDonald,D.; Bayly,C.; Perrier,H.; Han,Y.; Giroux,A.(Merck Frosst Canada Inc.)
参考来源:EP 1021429; US 6020339; WO 9918095
📄 详细内容
合成路线:The Grignard reaction of 3-(cyclopentyloxy)-4-methoxybenzaldehyde (I) with vinylmagnesium bromide in THF gives the vinyl carbinol (II),which is oxidized with MnO2 in ethyl acetate yielding the propenone (III).The condensation of (III) with pyridine-2-carbaldehyde (IV) by means of 3-ethyl-5-(2-hydroxyethyl)-4-methyl-thiazolium bromide (ETB) and triethylamine affords the butanedione (V),which is finally cyclized to the target compound with p-toluenesulfonic acid in refluxing toluene.
参考文献标题:Substituted furans as inhibitors of the PDE4 enzyme
文献作者:Perrier,H.; Bayly,C.; Laliberte,F.; Huang,z.; Rasori,R.; Robichaud,A.; Girard,Y.; Macdonald,D.
参考来源:Bioorg Med Chem Lett 1999,9(3),323