【结 构 式】 |
【分子编号】65262 【品名】 【CA登记号】 |
【 分 子 式 】C10H15BrN2O 【 分 子 量 】259.14598 【元素组成】C 46.35% H 5.83% Br 30.83% N 10.81% O 6.17% |
合成路线1
该中间体在本合成路线中的序号:(V)Vilsmeier reaction of 4-methoxy-3-pyrrolin-2-one (I) with phosphoryl bromide and N,N-dimethylformamide, followed by basic hydrolysis, provides 5-bromo-3-methoxypyrrole-2-carbaldehyde (II), which is then subjected to Suzuki coupling with 1-Boc-2-indoleboronic acid (III) to afford the indolyl pyrrolealdehyde (IV). In a related method, intermediate (IV) is prepared by reaction of pyrrolinone (I) with phosphoryl bromide and diethylformamide, followed by Suzuki coupling of the resulting bromopyrrole (V) with the indoleboronic acid (III) and basic enamine hydrolysis. The title compound is then obtained by simultaneous condensation and deprotection of pyrrole aldehyde (IV) with 2,4-dimethylpyrrole (VI) in methanolic hydrogen chloride (1). Scheme 1.
【1】 Attardo, G., Dairi, K., Lavallee, J.-F., Rioux, E., Tripathy, S. (Gemin X Biotechnologies, Inc.). Triheterocyclic compounds, compositions, and methods for treating cancer or viral diseases. EP 1644363, JP 2007502845, US 2005014802, WO 2004106328. |
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) | 65258 | 4-methoxy-3-pyrrolin-2-one | C5H7NO2 | 详情 | 详情 | |
(II) | 65259 | 5-bromo-3-methoxypyrrole-2-carbaldehyde | C6H6BrNO2 | 详情 | 详情 | |
(III) | 65260 | 1-Boc-2-indoleboronic acid; N-Boc-indole-2-boronic acid; 1-(tert-Butoxycarbonyl)-1H-indol-2-ylboronic acid | 213318-44-6 | C13H16BNO4 | 详情 | 详情 |
(IV) | 65261 | C19H20NO4 | 详情 | 详情 | ||
(V) | 65262 | C10H15BrN2O | 详情 | 详情 | ||
(VI) | 51236 | 2,4-Dimethylpyrrole | 625-82-1 | C6H9N | 详情 | 详情 |