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【结 构 式】 
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【分子编号】46831 【品名】N-(4-bromo-2-fluorophenyl)-2,2-dimethylpropanamide 【CA登记号】 |
【 分 子 式 】C11H13BrFNO 【 分 子 量 】274.1327632 【元素组成】C 48.2% H 4.78% Br 29.15% F 6.93% N 5.11% O 5.84% |
合成路线1
该中间体在本合成路线中的序号：(XV)Synthesis of intermediate (XVII): Coupling of 4-bromo-2-fluoroaniline (XIV) with pivaloyl chloride (VI) in pyridine affords N-protected substituted aniline (XV), which is then treated with 1-ethoxyvinyltributyltin (XVI) and bis(triphenylphosphine) palladium chloride (PdCl2(PPh3)2) in toluene to provide acetophenone derivative (XVII). Coupling of intermediates (XI) and (XVII): Ethyl benzoate (XI) is treated with NaH and added to a solution of acetophenone (XVII) in refluxing toluene/dioxane to furnish benzopyranone (XVIII), which is finally deprotected with HCl in dioxane to give the desired product.
| 【1】 Akama, T.; et al.; Synthesis of an ethyl 6-amino-3,5-difluorosalicylate derivative by sequential regioselective direct ortho-metalation; a practical synthesis of 4',5-diamino-3',6,8-trifluoroflavone, a potent antitumor agent. Synthesis 1997, 1446. |
| 【2】 Saito, H.; Ishida, H.; Akama, T.; Kimura, U.; Gomi, K.; Structure-activity relationships of the 7-substituents of 5,4'-diamino-6,8,3'-trifluoroflavone, a potent antitumor agent. J Med Chem 1998, 41, 12, 2056. |
| 【3】 Akama, T.; Ikeda, S.; Ishida, H.; Kimura, U.; Gomi, K.; Saito, H. (Kyowa Hakko Kogyo Co., Ltd.); 5-Aminoflavone derivs., their preparation and their use as antibacterial, anti-estrogenic and/or antitumor agent. EP 0638566; JP 1995109268 . |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (VI) | 13597 | 2,2-Dimethylpropanoyl chloride; Pivaloyl chloride | 3282-30-2 | C5H9ClO | 详情 | 详情 |
| (XI) | 46828 | ethyl 2-[(2,2-dimethylpropanoyl)amino]-3,5-difluoro-4-methyl-6-(tetrahydro-2H-pyran-2-yloxy)benzoate | C20H27F2NO5 | 详情 | 详情 | |
| (XIV) | 14723 | 4-Bromo-2-fluorophenylamine; 4-Bromo-2-fluoroaniline | 367-24-8 | C6H5BrFN | 详情 | 详情 |
| (XV) | 46831 | N-(4-bromo-2-fluorophenyl)-2,2-dimethylpropanamide | C11H13BrFNO | 详情 | 详情 | |
| (XVI) | 19760 | ethyl 1-(tributylstannyl)vinyl ether; tributyl(1-ethoxyvinyl)stannane | 97674-02-7 | C16H34OSn | 详情 | 详情 |
| (XVII) | 46832 | N-(4-acetyl-2-fluorophenyl)-2,2-dimethylpropanamide | C13H16FNO2 | 详情 | 详情 | |
| (XVIII) | 46833 | N-(4-[5-[(2,2-dimethylpropanoyl)amino]-6,8-difluoro-7-methyl-4-oxo-4H-chromen-2-yl]-2-fluorophenyl)-2,2-dimethylpropanamide | C26H27F3N2O4 | 详情 | 详情 |