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【结 构 式】 
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【药物名称】AU-254 【化学名称】6-Methoxy-3-methyl-1-(2-methylphenyl)-1H-pyrrolo[3,2-c]quinoline 【CA登记号】 【 分 子 式 】C20H18N2O 【 分 子 量 】302.37926 |
【开发单位】Korea Res. Inst. Chem. Technol. (Originator) 【药理作用】Antiulcer Drugs, Gastric Antisecretory Drugs, GASTROINTESTINAL DRUGS, H+/K+-ATPase Inhibitors |
合成路线1
The title compound was prepared by two related ways from 3-iodo-8-methoxy-4-(2-methylphenyl)aminoquinoline (I). Alkylationof (I) with allyl bromide (II) and NaH afforded the N-allyl amine (III). Subsequent intramolecular palladium-catalyzed Heck reaction in (III) produced the title pyrroloquinoline. In an alternative procedure, the intermolecular palladium-catalyzed heteroannulation of (I) with 1-trimethylsilylpropyne (IV) gave the silyl pyrroloquinoline (V), which was finally desilylated by means of trifluoroacetic acid.
| 【1】 Yum, E.K.; et al.; Synthesis and pharmacological profile of 1-aryl-3-substituted pyrrolo[3,2-c]quinolones. Bioorg Med Chem Lett 1999, 9, 19, 2819. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (I) | 34558 | 3-iodo-8-methoxy-N-(2-methylphenyl)-4-quinolinamine; N-(3-iodo-8-methoxy-4-quinolinyl)-N-(2-methylphenyl)amine | C17H15IN2O | 详情 | 详情 | |
| (II) | 11463 | 3-Bromo-1-propene; 3-Bromopropene；allyl bromide | 106-95-6 | C3H5Br | 详情 | 详情 |
| (III) | 34559 | N-allyl-3-iodo-8-methoxy-N-(2-methylphenyl)-4-quinolinamine; N-allyl-N-(3-iodo-8-methoxy-4-quinolinyl)-N-(2-methylphenyl)amine | C20H19IN2O | 详情 | 详情 | |
| (IV) | 34560 | trimethyl(1-propynyl)silane | 6224-91-5 | C6H12Si | 详情 | 详情 |