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【结 构 式】 
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【分子编号】33636 【品名】5H-chromeno[2,3-b]pyridin-5-ol 【CA登记号】 |
【 分 子 式 】C12H9NO2 【 分 子 量 】199.209 【元素组成】C 72.35% H 4.55% N 7.03% O 16.06% |
合成路线1
该中间体在本合成路线中的序号：(VII)The reduction of 5-oxo-5H[1]benzopyrane[2,3-b]pyridine (VI) affords 5-hydroxy-5H[1]benzopyrane[2,3-b]pyridine (VII), which is reduced again with refluxing isopropanol and HCl giving 5H[1]benzopyrane[2,3b]pyridine (VIII). This product is chloromethylated with HCHO and HCl in H2SO4 to yield 7-chloromethyl-5H[1]benzopyrane[2,3-b]pyridine (IX), which is treated with KCN in DMF-water to afford 7-cyanomethyl-5H[1]benzopyrane[2,3-b]pyridine (X). The reaction of (X) with diethyl carbonate (A) in ethanol containing sodium ethoxide gives ethyl 2-cyano-2-(5H[1]benzopyrano[2,3-b]pyridine-7-yl)acetate (XI), which, without isolation, is methylated with MeI to ethyl 2-cyano-2-(5H[1]-benzopyrano[2,3-b]pyridin-7-yl)propionate (XII). Finally, (XII) is hydrolyzed and decarboxylated with dry HCl in refluxing acetic acid.
| 【1】 Kato, Y.; et al.; Studies on anti-inflammatory agents. XXXII. Absorption, excretion, distribution and metabolism of 2-(5H-[1]-benzopyrano[2,3-b]pyridin-7-yl)propionic acid (Y-8004) in rats and mice. Yakugaku Zasshi 1976, 96, 819. |
| 【2】 Takanori, O.; et al.; Substituted alkanoic acids and derivatives. DE 2337052; FR 2193593; GB 1403487; US 3931205 . |
| 【3】 Nakanishi, M.; et al.; JP 7493398 . |
| 【4】 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 |
| (VI) | 33635 | 5H-chromeno[2,3-b]pyridin-5-one | C12H7NO2 | 详情 | 详情 | |
| (VII) | 33636 | 5H-chromeno[2,3-b]pyridin-5-ol | C12H9NO2 | 详情 | 详情 | |
| (VIII) | 33637 | 5H-chromeno[2,3-b]pyridine | C12H9NO | 详情 | 详情 | |
| (IX) | 33638 | 7-(chloromethyl)-5H-chromeno[2,3-b]pyridine | C13H10ClNO | 详情 | 详情 | |
| (X) | 33639 | 2-(5H-chromeno[2,3-b]pyridin-7-yl)acetonitrile | C14H10N2O | 详情 | 详情 | |
| (XI) | 33640 | ethyl 2-(5H-chromeno[2,3-b]pyridin-7-yl)-2-cyanoacetate | C17H14N2O3 | 详情 | 详情 | |
| (XII) | 33641 | ethyl 2-(5H-chromeno[2,3-b]pyridin-7-yl)-2-cyanopropanoate | C18H16N2O3 | 详情 | 详情 |