|
【结 构 式】 
|
【分子编号】47910 【品名】N-(tert-butyl)-4-[3-[(trimethylsilyl)oxy]propyl]-1H-imidazole-1-carboxamide 【CA登记号】 |
【 分 子 式 】C14H27N3O2Si 【 分 子 量 】297.4729 【元素组成】C 56.53% H 9.15% N 14.13% O 10.76% Si 9.44% |
合成路线1
该中间体在本合成路线中的序号：(II)The protection of 3-(1H-imidazol-4-yl)-1-propanol (I) according to known techniques gives (II), which is condensed with 4-iodobenzyl bromide (III) by means of ammonia in acetonitrile, yielding 3-[1-(4-iodobenzyl)-1H-imidazol-5-yl)-1-propanol (IV). The reaction of (IV) with SOCl2 in dichloromethane affords the corresponding chloro derivative (V), which is cyclized by means of LDA and TMEDA in THF, affording 5-(4-iodophenyl)-5,6,7,8-tetrahydroimidazo[1,5-a]pyridine (VI). Finally, this compound is treated with (14C)-KCN and palladium tetrakis(triphenylphosphine) in refluxing THF.
| 【1】 Markus, B.; Jones, L.; Duelfer, T.; Ray, T.; Wu, A.; Allentoff, A.J.; Ciszewska, G.; Palladium-catalyzed aryl cyanations with [C-14]KCN: Synthesis of C-14-labelled fadrozole, a potent aromatase inhibitor. J Label Compd Radiopharm 2000, 43, 11, 1075. |
| 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) | 21245 | 3-(1H-imidazol-4-yl)-1-propanol | C6H10N2O | 详情 | 详情 | |
| (II) | 47910 | N-(tert-butyl)-4-[3-[(trimethylsilyl)oxy]propyl]-1H-imidazole-1-carboxamide | C14H27N3O2Si | 详情 | 详情 | |
| (III) | 39980 | 1-(bromomethyl)-4-iodobenzene | 16004-15-2 | C7H6BrI | 详情 | 详情 |
| (IV) | 39979 | 3-[1-(4-iodobenzyl)-1H-imidazol-5-yl]-1-propanol | C13H15IN2O | 详情 | 详情 | |
| (V) | 39981 | 5-(3-chloropropyl)-1-(4-iodobenzyl)-1H-imidazole | C13H14ClIN2 | 详情 | 详情 | |
| (VI) | 39982 | 5-(4-iodophenyl)-5,6,7,8-tetrahydroimidazo[1,5-a]pyridine | C13H13IN2 | 详情 | 详情 |