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【结 构 式】 
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【分子编号】36351 【品名】[1-(4-bromobenzyl)-2-butyl-4-chloro-1H-imidazol-5-yl]methanol 【CA登记号】 |
【 分 子 式 】C15H18BrClN2O 【 分 子 量 】357.6775 【元素组成】C 50.37% H 5.07% Br 22.34% Cl 9.91% N 7.83% O 4.47% |
合成路线1
该中间体在本合成路线中的序号：(IV)The condensation of 2-butyl-4-chloroimidazole-5-carbaldehyde (I) with 4-bromobenzyl bromide (II) by means of K2CO3 in dimethylacetamide gives 1-(4-bromobenzyl)-2-butyl-4-chloroimidazole-5-carbaldehyde (III), which is reduced with NaBH4 in methanol yielding the corresponding carbinol (IV). The condensation of (IV) with the phenylboronic acid (VI) by means of Pd(OAc)2 and PPh3 affords the biphenyl derivative (VI), which is finally detritylated with H2SO4 in acetonitrile. The intermediate phenylboronic acid (V) has been obtained as follows: The protection of 5-phenyltetrazole (VII) with trityl chloride and TEA in THF gives 5-phenyl-2-(triphenylmethyl)tetrazole (VII), which is then treated with isopropyl borate and BuLi in THF.
| 【1】 Larsen, R.D.; et al.; Efficient synthesis of losartan, a nonpeptide angiotensin II receptor antagonist. J Org Chem 1994, 59, 21, 6391. |
| 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) | 13925 | 2-Butyl-4-chloro-1H-imidazole-5-carbaldehyde | 83857-96-9 | C8H11ClN2O | 详情 | 详情 |
| (II) | 16109 | 1-bromo-4-(bromomethyl)benzene; 4-Bromobenzyl bromide | 589-15-1 | C7H6Br2 | 详情 | 详情 |
| (III) | 36350 | 1-(4-bromobenzyl)-2-butyl-4-chloro-1H-imidazole-5-carbaldehyde | C15H16BrClN2O | 详情 | 详情 | |
| (IV) | 36351 | [1-(4-bromobenzyl)-2-butyl-4-chloro-1H-imidazol-5-yl]methanol | C15H18BrClN2O | 详情 | 详情 | |
| (V) | 36352 | 2-(2-trityl-2H-1,2,3,4-tetraazol-5-yl)phenylboronic acid | C26H21BN4O2 | 详情 | 详情 | |
| (VI) | 13932 | (2-Butyl-4-chloro-1-[[2'-(2-trityl-2H-1,2,3,4-tetraazol-5-yl)[1,1'-biphenyl]-4-yl]methyl]-1H-imidazol-5-yl)methanol | C41H37ClN6O | 详情 | 详情 | |
| (VII) | 36353 | 5-phenyl-2H-1,2,3,4-tetraazole | 18039-42-4 | C7H6N4 | 详情 | 详情 |
| (VIII) | 36354 | 5-phenyl-2-trityl-2H-1,2,3,4-tetraazole | C26H20N4 | 详情 | 详情 |