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【结 构 式】 
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【分子编号】33750 【品名】[(1S)-8-bromo-1-(bromomethyl)-5-hydroxy-7-methyl-1,6-dihydropyrrolo[3,2-e]indol-3(2H)-yl](5,6,7-trimethoxy-1H-indol-2-yl)methanone 【CA登记号】 |
【 分 子 式 】C24H23Br2N3O5 【 分 子 量 】593.27184 【元素组成】C 48.59% H 3.91% Br 26.94% N 7.08% O 13.48% |
合成路线1
该中间体在本合成路线中的序号：(XII)Decarboxylation of (IX) in refluxing bromobenzene yielded (X), which was converted to the 3-bromoindole (XI) by reaction with N-bromosuccinimide in the presence of silicagel. Desilylation of (XI) with tetrabutylammonium fluoride gave phenol (XII), and further intramolecular cyclization of (XII) with simultaneous amide hydrolysis by treatment with NaOMe produced the cyclopropyl cyclohexadienone (XIII). Finally, the 4-methoxycinnamoyl group was introduced in (XIII) by condensation with the 4-nitrophenyl ester (XIV) in the presence of NaH at -20 C.
| 【1】 Okabe, M.; Tamaoki, T.; Saito, H.; Okamoto, A.; Amishiro, N.; Murakata, C.; Synthesis and antitumor activity of duocarmycin derivatives: Modification of segment-A of A-ring pyrrole compounds. J Med Chem 1999, 42, 15, 2946-60. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (IX) | 33747 | (8S)-8-(bromomethyl)-4-[[tert-butyl(dimethyl)silyl]oxy]-2-methyl-6-[(5,6,7-trimethoxy-1H-indol-2-yl)carbonyl]-3,6,7,8-tetrahydropyrrolo[3,2-e]indole-1-carboxylic acid | C31H38BrN3O7Si | 详情 | 详情 | |
| (X) | 33748 | [(1S)-1-(bromomethyl)-5-[[tert-butyl(dimethyl)silyl]oxy]-7-methyl-1,6-dihydropyrrolo[3,2-e]indol-3(2H)-yl](5,6,7-trimethoxy-1H-indol-2-yl)methanone | C30H38BrN3O5Si | 详情 | 详情 | |
| (XI) | 33749 | [(1S)-8-bromo-1-(bromomethyl)-5-[[tert-butyl(dimethyl)silyl]oxy]-7-methyl-1,6-dihydropyrrolo[3,2-e]indol-3(2H)-yl](5,6,7-trimethoxy-1H-indol-2-yl)methanone | C30H37Br2N3O5Si | 详情 | 详情 | |
| (XII) | 33750 | [(1S)-8-bromo-1-(bromomethyl)-5-hydroxy-7-methyl-1,6-dihydropyrrolo[3,2-e]indol-3(2H)-yl](5,6,7-trimethoxy-1H-indol-2-yl)methanone | C24H23Br2N3O5 | 详情 | 详情 | |
| (XIII) | 33751 | (3bR,4aS)-3-bromo-2-methyl-4,4a,5,6-tetrahydrocyclopropa[c]pyrrolo[3,2-e]indol-8(1H)-one | C12H11BrN2O | 详情 | 详情 | |
| (XIV) | 33752 | 4-nitrophenyl (E)-3-(4-methoxyphenyl)-2-propenoate | C16H13NO5 | 详情 | 详情 |