4-(5-methoxy-1H-indol-3-yl)-4-oxobutyric acid -Drug Synthesis Database

【结构式】

【分子编号】30614

【品名】4-(5-methoxy-1H-indol-3-yl)-4-oxobutyric acid

【CA登记号】

【分子式】C₁₃H₁₃NO₄

【分子量】247.25056

【元素组成】C 63.15% H 5.3% N 5.66% O 25.88%

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)

A new synthesis of roxindole has been described: The condensation of 5-methoxyindole (I) with succinic anhydride (II) by means of methylmagnesium bromide in hot anisole gives the 4-oxobutyric acid derivative (III), which is condensed with the 4-phenyltetrahydropyridine (IV) by means of EDC and DIPEA in DMF yielding the butanedione (V). The reduction of (V) with LiAlH4 in refluxing THF affords intermediate (VI), which is finally demethylated with DIBAH in refluxing toluene.

参考文献中间体

合成目标

【1】 Lange, J.H.M.; et al.; A straightforward synthetic approach for roxindole. Bioorg Med Chem Lett 1999, 9, 7, 1055.

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)	25902	1H-Indol-5-yl methyl ether; 5-Methoxy-1H-indole; 5-Methoxyindole	1006-94-6	C₉H₉NO	详情	详情
(II)	11291	Dihydro-2,5-furandione; Succinic anhydride	108-30-5	C₄H₄O₃	详情	详情
(III)	30614	4-(5-methoxy-1H-indol-3-yl)-4-oxobutyric acid		C₁₃H₁₃NO₄	详情	详情
(IV)	13002	4-Phenyl-1,2,3,6-tetrahydropyridine; 1,2,3,6-Tetrahydro-4-phenyl-pyridine	10338-69-9	C₁₁H₁₃N	详情	详情
(V)	30615	1-(5-methoxy-1H-indol-3-yl)-4-[4-phenyl-3,6-dihydro-1(2H)-pyridinyl]-1,4-butanedione		C₂₄H₂₄N₂O₃	详情	详情
(VI)	12999	5-Methoxy-3-[4-[4-phenyl-3,6-dihydro-1(2H)-pyridinyl]butyl]-1H-indole; Methyl 3-[4-[4-phenyl-3,6-dihydro-1(2H)-pyridinyl]butyl]-1H-indol-5-yl ether		C₂₄H₂₈N₂O	详情	详情

Extended Information