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【结 构 式】 
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【分子编号】33645 【品名】7-methyl-5H-chromeno[2,3-b]pyridin-5-one 【CA登记号】 |
【 分 子 式 】C13H9NO2 【 分 子 量 】211.22 【元素组成】C 73.92% H 4.29% N 6.63% O 15.15% |
合成路线1
该中间体在本合成路线中的序号：(XVI)The bromination of 7-methyl-5-oxo-5H[1]benzopyrane[2,3-b]pyridine (XVI) with NBS in CCl4 gives 7-bromomethyl-5-oxo-5H[1]benzopyrane[2,3-b] pyridine (XVII), which is treated with NaCN in DMF yielding 7-cyanomethyl-5-oxo-5H[1]benzopyrane[2,3b]pyridine (XVIII). The reaction of (XVIII) with diethyl carbonate (A) by means of sodium ethoxide in ethanol affords ethyl 2-cyano-2-(5-oxo-5H[1]benzopyrane[2,3b]pyridine-7-yl)acetate (XIX), which, without isolation, is methylated with MeI giving ethyl 2-cyano-2-(5-oxo-5H[1]benzopyrane[2,3b]pyridine-7-yl)propionate (XX); finally this product is hydrolyzed and decarboxylated with dry HCl in refluxing acetic acid. An alternative way starting from the cyano derivative (XVIII) is its methylation with NaNH2 and MeI giving 7-(1-cyanoethyl)-5-oxo-5H[1]benzopyrane[2,3-b]pyridine (XXI), which is hydrolyzed with dry HCl in refluxing acetic acid.
| 【1】 Nakanishi, M.; Oe, T.; Tsuruda, M.; Substituted alkanoic acids and derivatives. DE 2337052; FR 2193593; GB 1403487; US 3931205 . |
| 【2】 Nakanishi, M.; et al.; JP 7535196 . |
| 【3】 Roberts, P.; Castaner, J.; Y 8004. Drugs Fut 1977, 2, 3, 217. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (A) | 17470 | diethyl carbonate; diethylcarbonate | 105-58-8 | C5H10O3 | 详情 | 详情 |
| (I) | 33630 | 2-(5-oxo-5H-chromeno[2,3-b]pyridin-7-yl)propionic acid | C15H11NO4 | 详情 | 详情 | |
| (XVI) | 33645 | 7-methyl-5H-chromeno[2,3-b]pyridin-5-one | C13H9NO2 | 详情 | 详情 | |
| (XVII) | 33646 | 7-(bromomethyl)-5H-chromeno[2,3-b]pyridin-5-one | C13H8BrNO2 | 详情 | 详情 | |
| (XVIII) | 33647 | 2-(5-oxo-5H-chromeno[2,3-b]pyridin-7-yl)acetonitrile | C14H8N2O2 | 详情 | 详情 | |
| (XIX) | 33648 | ethyl 2-cyano-2-(5-oxo-5H-chromeno[2,3-b]pyridin-7-yl)acetate | C17H12N2O4 | 详情 | 详情 | |
| (XX) | 33649 | ethyl 2-cyano-2-(5-oxo-5H-chromeno[2,3-b]pyridin-7-yl)propanoate | C18H14N2O4 | 详情 | 详情 | |
| (XXI) | 33650 | 2-(5-oxo-5H-chromeno[2,3-b]pyridin-7-yl)propanenitrile | C15H10N2O2 | 详情 | 详情 |