N-allyl-3-iodo-8-methoxy-N-(2-methylphenyl)-4-quinolinamine; N-allyl-N-(3-iodo-8-methoxy-4-quinolinyl)-N-(2-methylphenyl)amine -Drug Synthesis Database

【结构式】

【分子编号】34559

【品名】N-allyl-3-iodo-8-methoxy-N-(2-methylphenyl)-4-quinolinamine; N-allyl-N-(3-iodo-8-methoxy-4-quinolinyl)-N-(2-methylphenyl)amine

【CA登记号】

【分子式】C₂₀H₁₉IN₂O

【分子量】430.28821

【元素组成】C 55.83% H 4.45% I 29.49% N 6.51% O 3.72%

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：(III)

The title compound was prepared by two related ways from 3-iodo-8-methoxy-4-(2-methylphenyl)aminoquinoline (I). Alkylationof (I) with allyl bromide (II) and NaH afforded the N-allyl amine (III). Subsequent intramolecular palladium-catalyzed Heck reaction in (III) produced the title pyrroloquinoline. In an alternative procedure, the intermolecular palladium-catalyzed heteroannulation of (I) with 1-trimethylsilylpropyne (IV) gave the silyl pyrroloquinoline (V), which was finally desilylated by means of trifluoroacetic acid.

参考文献中间体

合成目标

【1】 Yum, E.K.; et al.; Synthesis and pharmacological profile of 1-aryl-3-substituted pyrrolo[3,2-c]quinolones. Bioorg Med Chem Lett 1999, 9, 19, 2819.

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)	34558	3-iodo-8-methoxy-N-(2-methylphenyl)-4-quinolinamine; N-(3-iodo-8-methoxy-4-quinolinyl)-N-(2-methylphenyl)amine		C₁₇H₁₅IN₂O	详情	详情
(II)	11463	3-Bromo-1-propene; 3-Bromopropene；allyl bromide	106-95-6	C₃H₅Br	详情	详情
(III)	34559	N-allyl-3-iodo-8-methoxy-N-(2-methylphenyl)-4-quinolinamine; N-allyl-N-(3-iodo-8-methoxy-4-quinolinyl)-N-(2-methylphenyl)amine		C₂₀H₁₉IN₂O	详情	详情
(IV)	34560	trimethyl(1-propynyl)silane	6224-91-5	C₆H₁₂Si	详情	详情

Extended Information