2a-(4-bromobutyl)-2a,3,4,5-tetrahydrobenzo[cd]indol-2(1H)-one -Drug Synthesis Database

【结构式】

【分子编号】25591

【品名】2a-(4-bromobutyl)-2a,3,4,5-tetrahydrobenzo[cd]indol-2(1H)-one

【CA登记号】

【分子式】C₁₅H₁₈BrNO

【分子量】308.21806

【元素组成】C 58.45% H 5.89% Br 25.92% N 4.54% O 5.19%

与该中间体有关的原料药合成路线共 2 条

合成路线1 合成路线2

合成路线1

该中间体在本合成路线中的序号：(III)

Tetrahydrobenzindole (I) was alkylated with 1,4-dibromobutane (II) in the presence of NaH to afford the bromobutyl derivative (III). This was then condensed with 4-phenyltetrahydropyridine (IV) to yield the title compound.

参考文献中间体

合成目标

【1】 Kikuchi, C.; et al.; Tetrahydrobenzindoles: Selective antagonists of the 5-HT7 receptor. J Med Chem 1999, 42, 4, 533.

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)	25590	2a,3,4,5-tetrahydrobenzo[cd]indol-2(1H)-one	96933-21-0	C₁₁H₁₁NO	详情	详情
(II)	11883	1,4-Dibromobutane; 1,4-Butylene bromide	110-52-1	C₄H₈Br₂	详情	详情
(III)	25591	2a-(4-bromobutyl)-2a,3,4,5-tetrahydrobenzo[cd]indol-2(1H)-one		C₁₅H₁₈BrNO	详情	详情
(IV)	25592	4-phenyl-1,2,3,6-tetrahydropyridine hydrochloride	1191-50-0	C₁₁H₁₄ClN	详情	详情

合成路线2

该中间体在本合成路线中的序号：(VI)

Tetrahydrobenzo[cd]indol-2-one (IV) is selectively alkylated at position 2a with 1,4-dibromobutane (V) in the presence of NaH to provide the bromobutyl derivative (VI). Then, condensation of bromide (VI) with amine (III) employing K2CO3 in DMF leads to the title compound.

参考文献中间体

合成目标

【1】 Kikuchi, C.; et al.; 2a-[4-(Tetrahydropyridondol-2-yl)butyl]tetrahydrobenzindole derivatives: New selective antagonists of the 5-hydroxytryptamine7 receptor. J Med Chem 2002, 45, 11, 2197.
【2】 Koyama, M.; Okuno, M.; Hiranuma, T.; Ando, T.; Fuji, K.; Ushiroda, O.; Kikuchi, C.; Shiiyama, M.; Satoh, E. (Meiji Seika Kaisha, Ltd.); Tetrahydrobenzindole derivs.. EP 1057814; JP 1999189585; US 6498251; WO 9933804 .

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(III)	60193	N,N-dimethyl-1,2,3,4-tetrahydro-9H-beta-carboline-9-carboxamide		C₁₄H₁₇N₃O	详情	详情
(IV)	25590	2a,3,4,5-tetrahydrobenzo[cd]indol-2(1H)-one	96933-21-0	C₁₁H₁₁NO	详情	详情
(V)	11883	1,4-Dibromobutane; 1,4-Butylene bromide	110-52-1	C₄H₈Br₂	详情	详情
(VI)	25591	2a-(4-bromobutyl)-2a,3,4,5-tetrahydrobenzo[cd]indol-2(1H)-one		C₁₅H₁₈BrNO	详情	详情

Extended Information