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【结 构 式】 
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【分子编号】28983 【品名】8-bromo-N-ethyl-3,4-dimethoxy-9-phenanthrenamine 【CA登记号】 |
【 分 子 式 】C18H18BrNO2 【 分 子 量 】360.25046 【元素组成】C 60.01% H 5.04% Br 22.18% N 3.89% O 8.88% |
与该中间体有关的原料药合成路线共 1 条
合成路线1
该中间体在本合成路线中的序号：(I)The acylation of 9-ethylamino-8-bromo-3,4-dimethoxyphenanthrene (I) with butyryl chloride (II) in CH2Cl2 gives 9-(N-ethyl-N-butyrylamino)-8-bromo-3,4-dimethoxyphenanthrene (III), which is cyclized by means of butyllithium in THF yielding 5-ethyl-4,5-dihydro-9,10-dimethoxy-4-n-propyldibenz[cd,f]indole-4-ol (IV). The reduction of (IV) with Zn-HgCl2 in refluxing ethanol water affords 5-ethyl-4,5,5a,6-tetrahydro-9,10-diethoxy-4-n-propyldibenz[cd,f]indole (V), which is finally demethylated by means of refluxing aqueous 47% HBr.
| 【1】 Giger, R.K.A. (Novartis AG); Nouveaux derives du dibenz[cd,f]indole, leur preparation et leur application comme medicaments. DE 3124086; FR 2485530; FR 2510996; WO 8200143 . |
| 【2】 Castaner, J.; Serradell, M.N.; 201678. Drugs Fut 1985, 10, 2, 99. |
| 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) | 28983 | 8-bromo-N-ethyl-3,4-dimethoxy-9-phenanthrenamine | C18H18BrNO2 | 详情 | 详情 | |
| (II) | 10792 | Butanoyl chloride; Butyryl chloride | 141-75-3 | C4H7ClO | 详情 | 详情 |
| (III) | 28984 | N-(8-bromo-3,4-dimethoxy-9-phenanthryl)-N-ethylbutanamide | C22H24BrNO3 | 详情 | 详情 | |
| (IV) | 28985 | (4R)-5-ethyl-9,10-dimethoxy-4-propyl-4,5-dihydrodibenzo[cd,f]indol-4-ol | C22H25NO3 | 详情 | 详情 | |
| (V) | 28986 | (4S,5aR)-5-ethyl-10-methoxy-4-propyl-4,5,5a,6-tetrahydrodibenzo[cd,f]indol-9-yl methyl ether | C22H27NO2 | 详情 | 详情 |
Extended Information