TEI-4120
甲醇,[1-(2-乙氧基-1-甲基乙基)-2-甲基-1H-吲哚-3-基]苯基-Chemical Name: [1-(2-Ethoxy-1-methylethyl)-2-methyl-1H-indol-3-yl]phenylmethanone; 3-Benzoyl-N-(1-ethoxy-2-propyl)-2-methylindole; 3-Benzoyl-N-beta-ethoxyisopropyl-2-methylindole
CAS No. 77992-61-1
项目整合开发状态: Biological Testing
项目研究机构: Teijin (Originator)
合成路线:The cyclization of 2-acetonylcyclohexanone (I) with alanine ethyl ester (II) by means of sodium acetate in refluxing acetic acid gives ethyl 2-(4,5,6,7-tetrahydro-2-methylindol-1-yl)propionate (III),which is reduced with LiAlH4 in ether and acetylated with acetic anhydride in pyridine yielding 1-(1-acetoxy-2-propyl)-2-methyl-4,5,6,7-tetrahydroindole (IV).The benzoylation of (IV) with benzoic anhydride (V) and HI at 145 C affords 1-(1-acetoxy-2-propyl)-3-benzoyl-2-methyl-4,5,6,7-tetrahydroindole (VI),which is aromatized by treatment with 2,3-dichloro-5,6-dicyanobenzoquinone (VII) in refluxing dioxane to afford 1-(1-acetoxy-2-propyl)-3-benzoyl-2-methylindole (VIII) The hydrolysis of (VIII) with NaOH in methanol water gives 1-(1-hydroxy-2-propyl)-3-benzoyl-2-methylindole (IX),which is finally alkylated with ethyl bromide by means of NaH in dimethoxyethane.
📌 参考资料/链接：
参考文献标题:Acylated indole derivatives,processes for their preparation and pharmaceutical compositions and drugs comprising them
文献作者:Oba,T.; et al.(Teijin Ltd.)
参考来源:EP 0022634; JP 8107762; JP 81108765; JP 8139068; JP 8151452; JP 8163960
📄 详细内容
合成路线:The cyclization of 2-acetonylcyclohexanone (I) with alanine ethyl ester (II) by means of sodium acetate in refluxing acetic acid gives ethyl 2-(4,5,6,7-tetrahydro-2-methylindol-1-yl)propionate (III),which is reduced with LiAlH4 in ether and acetylated with acetic anhydride in pyridine yielding 1-(1-acetoxy-2-propyl)-2-methyl-4,5,6,7-tetrahydroindole (IV).The benzoylation of (IV) with benzoic anhydride (V) and HI at 145 C affords 1-(1-acetoxy-2-propyl)-3-benzoyl-2-methyl-4,5,6,7-tetrahydroindole (VI),which is aromatized by treatment with 2,3-dichloro-5,6-dicyanobenzoquinone (VII) in refluxing dioxane to afford 1-(1-acetoxy-2-propyl)-3-benzoyl-2-methylindole (VIII) The hydrolysis of (VIII) with NaOH in methanol water gives 1-(1-hydroxy-2-propyl)-3-benzoyl-2-methylindole (IX),which is finally alkylated with ethyl bromide by means of NaH in dimethoxyethane.
参考文献标题:TEI-4120
文献作者:Castar,J.; Serradell,M.N.; Owen,R.T.
参考来源:Drugs Fut 1985,10(2),129
产品链接: CAS No. 77992-61-1››