4-(1,2-dibromoethyl)phenyl methyl ether; 1-(1,2-dibromoethyl)-4-methoxybenzene -Drug Synthesis Database

【结构式】

【分子编号】44050

【品名】4-(1,2-dibromoethyl)phenyl methyl ether; 1-(1,2-dibromoethyl)-4-methoxybenzene

【CA登记号】

【分子式】C₉H₁₀Br₂O

【分子量】293.9858

【元素组成】C 36.77% H 3.43% Br 54.36% O 5.44%

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：(II)

The bromination of 4-methoxystyrene (I) with Br2 gives the alpha,beta-dibromo derivative (II), which by selective debromination with potassium tert-butoxide yields the tert-butyl ether (III). The condensation of (III) with 2-(2-chloro-3,4-dimethoxyphenyl)ethylamine (IV) affords the secondary amine (V), which is deprotected with H2SO4 to provide the substituted ethanolamine (VI). The cyclization of (VI) by means of Ms-OH and trifluoroacetic acid gives the 3-benzazepine (VII), which is finally demethylated with BBr3 and treated with methanesulfonic acid to afford the target mesylate.

参考文献中间体

合成目标

【1】 Hieble, J.P.; Wilson III, J.W.; Weinstock, J.; The chemistry and pharmacology of 3-benzazepines derivatives. Drugs Fut 1985, 10, 8, 645.
【2】 US 4321195 .

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)	44049	1-methoxy-4-vinylbenzene; methyl 4-vinylphenyl ether	637-69-4	C₉H₁₀O	详情	详情
(II)	44050	4-(1,2-dibromoethyl)phenyl methyl ether; 1-(1,2-dibromoethyl)-4-methoxybenzene		C₉H₁₀Br₂O	详情	详情
(III)	44051	4-[2-bromo-1-(tert-butoxy)ethyl]phenyl methyl ether; 1-[2-bromo-1-(tert-butoxy)ethyl]-4-methoxybenzene		C₁₃H₁₉BrO₂	详情	详情
(IV)	42037	2-chloro-3,4-dimethoxyphenethylamine; 2-(2-chloro-3,4-dimethoxyphenyl)-1-ethanamine	67287-36-9	C₁₀H₁₄ClNO₂	详情	详情
(V)	44052	2-(tert-butoxy)-N-(2-chloro-3,4-dimethoxyphenethyl)-2-(4-methoxyphenyl)-1-ethanamine; N-[2-(tert-butoxy)-2-(4-methoxyphenyl)ethyl]-N-(2-chloro-3,4-dimethoxyphenethyl)amine		C₂₃H₃₂ClNO₄	详情	详情
(VI)	31702	2-[(2-chloro-3,4-dimethoxyphenethyl)amino]-1-(4-methoxyphenyl)-1-ethanol		C₁₉H₂₄ClNO₄	详情	详情
(VII)	31704	4-(6-chloro-7,8-dimethoxy-2,3,4,5-tetrahydro-1H-3-benzazepin-1-yl)phenyl methyl ether; 6-chloro-7,8-dimethoxy-1-(4-methoxyphenyl)-2,3,4,5-tetrahydro-1H-3-benzazepine		C₁₉H₂₂ClNO₃	详情	详情

Extended Information