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【结 构 式】 
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【药物名称】 【化学名称】5-Bromo-3-[(4-fluorophenyl)(1H-imidazol-1-yl)methyl]-1-methyl-1H-indole 【CA登记号】 【 分 子 式 】C19H15BrFN3 【 分 子 量 】384.2539 |
【开发单位】Universität des Saarlandes (Originator) 【药理作用】Oncolytic Drugs, Aromatase Inhibitors |
合成路线1
The methylation of 5-bromo-1H-indole (I) with methyl iodide and NaH in DMSO gives the 1-methyl derivative (II), which is acylated with 4-fluorobenzoyl chloride (III) and AlCl3 in dichloromethane yielding the 3-acyl derivative (IV). The reduction of (IV) with NaBH4 in methanol affords the corresponding carbinol (V), which is finally treated with carbonyl diimidazole (VI) in THF.
| 【1】 Marchand, P.; Robert, J.-M.; Palzer, M.; Delovoye-Seiller, B.; Hartmann, R.W.; Le Baut, G.; Le Borgne, M.; New selective nonsteroidal aromatase inhibitors: Synthesis and inhibitory activity of 2, 3 or 5-(alpha-azolylbenzyl)-1H-indoles. Bioorg Med Chem Lett 1999, 9, 3, 333. |
| 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) | 13309 | 5-Bromo-1H-indole; 5-Bromoindole | 10075-50-0 | C8H6BrN | 详情 | 详情 |
| (II) | 29521 | 5-bromo-1-methyl-1H-indole | C9H8BrN | 详情 | 详情 | |
| (III) | 17263 | 4-fluorobenzoyl chloride | 403-43-0 | C7H4ClFO | 详情 | 详情 |
| (IV) | 29522 | (5-bromo-1-methyl-1H-indol-3-yl)(4-fluorophenyl)methanone | C16H11BrFNO | 详情 | 详情 | |
| (V) | 29523 | (5-bromo-1-methyl-1H-indol-3-yl)(4-fluorophenyl)methanol | C16H13BrFNO | 详情 | 详情 | |
| (VI) | 11353 | 1,1'-Carbonyldiimidazole; Di(1H-imidazol-1-yl)methanone; N,N-Carbonyldiimidazole; 1,1'-Carbonylbis(1H-imidazole) | 530-62-1 | C7H6N4O | 详情 | 详情 |
Extended Information