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【结 构 式】

【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%

与该中间体有关的原料药合成路线共 1 条

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
Extended Information