3-[5-(1H-indol-3-yl)-2-pyrazinyl]-1H-indole -Drug Synthesis Database

【结构式】

【分子编号】46766

【品名】3-[5-(1H-indol-3-yl)-2-pyrazinyl]-1H-indole

【CA登记号】

【分子式】C₂₀H₁₄N₄

【分子量】310.35812

【元素组成】C 77.4% H 4.55% N 18.05%

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：(V)

Reaction of indole (I) with chloroacetyl chloride (II) in the presence of pyridine in toluene afforded the chloro ketone (III). This was then treated with sodium azide in aqueous acetone to furnish the azido ketone (IV). Hydrogenation of (IV) over Pd/C in the presence of a catalytic amount of HOAc gave rise to 3,5-bisindolyl pyrazine (V). Finally, N-methylation of the indole rings with iodomethane and K2CO3 yielded the title compound.

参考文献中间体

合成目标

【1】 Jiang, B.; Gu, X.-H.; Syntheses and cytotoxicity evaluation of bis(indolyl)thiazole, bis(indolyl)pyrazinone and bis(indolyl)pyrazine: Analogues of cytotoxic marine bis(indole) alkaloid. Bioorg Med Chem 2000, 8, 2, 363.

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)	15292	Indole; 1H-indole	120-72-9	C₈H₇N	详情	详情
(II)	11296	2-Chloroacetyl chloride; Chloroacetic chloride	79-04-9	C₂H₂Cl₂O	详情	详情
(III)	46764	2-chloro-1-(1H-indol-3-yl)-1-ethanone		C₁₀H₈ClNO	详情	详情
(IV)	46765	2-azido-1-(1H-indol-3-yl)-1-ethanone		C₁₀H₈N₄O	详情	详情
(V)	46766	3-[5-(1H-indol-3-yl)-2-pyrazinyl]-1H-indole		C₂₀H₁₄N₄	详情	详情

Extended Information