2-(1H-pyrrol-1-yl)-3-pyridinol -Drug Synthesis Database

【结构式】

【分子编号】41979

【品名】2-(1H-pyrrol-1-yl)-3-pyridinol

【CA登记号】

【分子式】C₉H₈N₂O

【分子量】160.1754

【元素组成】C 67.49% H 5.03% N 17.49% O 9.99%

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)

1-(3-Hydroxy-2-pyridyl)pyrrole (III) was prepared by Paal-Knorr condensation of 2-amino-3-hydroxypyridine (I) with 2,5-dimethoxytetrahydrofuran (II). The O-alkylation of (II) with ethyl alpha-bromophenylacetate (IV) in the presence of NaH in THF furnished ether (V). Subsequent saponification of the ethyl ester group of (IV) gave rise to carboxylic acid (VI), that was cyclized to tricyclic ketone (VII) upon treatment with phosphorus pentachloride. Finally, alkylation of the corresponding potassium enolate of (VII) with ethyl iodide yielded the title compound.

参考文献中间体

合成目标

【1】 Morelli, E.; Campiani, G.; Fabbrini, M.; et al.; Pyrrolobenzoxazepinone derivatives as non-nucleoside HIV-1 RT inhibitors: Further structure-activity relationship studies and identification of more potent broad-spectrum HIV-1 RT inhibitors with antiviral activirty. J Med Chem 1999, 42, 21, 4462.

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)	37086	2-amino-3-pyridinol; 2-Amino-3-hydroxypyridine	16867-03-1	C₅H₆N₂O	详情	详情
(II)	12132	2,5-Dimethoxytetrahydrofuran; 5-Methoxytetrahydro-2-furanyl methyl ether	696-59-3	C₆H₁₂O₃	详情	详情
(III)	41979	2-(1H-pyrrol-1-yl)-3-pyridinol		C₉H₈N₂O	详情	详情
(IV)	41980	ethyl 2-bromo-2-phenylacetate	2882-19-1	C₁₀H₁₁BrO₂	详情	详情
(V)	41981	ethyl 2-phenyl-2-[[2-(1H-pyrrol-1-yl)-3-pyridinyl]oxy]acetate		C₁₉H₁₈N₂O₃	详情	详情
(VI)	41982	2-phenyl-2-[[2-(1H-pyrrol-1-yl)-3-pyridinyl]oxy]acetic acid		C₁₇H₁₄N₂O₃	详情	详情
(VII)	41983	6-phenylpyrido[3,2-b]pyrrolo[1,2-d][1,4]oxazepin-7(6H)-one		C₁₇H₁₂N₂O₂	详情	详情

Extended Information