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【结 构 式】 
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【分子编号】62865 【品名】2-(5-ethyl-2-pyridinyl)ethyl 4-methylbenzenesulfonate 【CA登记号】 |
【 分 子 式 】C16H19NO3S 【 分 子 量 】305.3978 【元素组成】C 62.93% H 6.27% N 4.59% O 15.72% S 10.5% |
合成路线1
该中间体在本合成路线中的序号：(II)This compound has been obtained by several different methods. The reaction of 2-(5-ethyl-2-pyridyl)ethanol (I) with Ts-Cl and NaOH in THF gives the corresponding tosylate (II), which is condensed with 4-hydroxybenzaldehyde (IV) by means of BnNBu3Cl and NaOH or K2CO3 to yield the aryl ether (V) (1-3). The condensation of (V) with thiazolidine-2,4-dione (VI) in refluxing ethanol affords the 5-benzylidenethiazolidinedione (VII), which is finally reduced with H2 over Pd/C in DMF or dioxane. The reaction of 2-(5-ethyl-2-pyridyl)ethanol (I) with Ms-Cl and TEA in dichloromethane THF gives the corresponding mesylate (III), which is condensed with 4-hydroxybenzaldehyde (IV) by means of K2CO3 to yield the already reported aryl ether (V). The condensation of 2-(5-ethyl-2-pyridyl)ethanol (I) with 4-fluorobenzonitrile (VIII) by means of NaH gives 4-[2-(5-ethyl-2-pyridyl)ethoxy]benzonitrile (IX), which is reduced with RaNi and HCOOH to yield the already reported 4-ethoxybenzaldehyde derivative (V).
| 【1】 Saito, Y.; Yamashita, M.; Mizufune, H. (Takeda Chemical Industries, Ltd.); Process for preparing 4-(2-(2-pyridyl)ethoxy)benzaldehyde derivs.. EP 0816340 . |
| 【2】 Mizuno, Y.; Arita, M. (Takeda Chemical Industries, Ltd.); Method for producing ethers. EP 0506273 . |
| 【3】 Meguro, K.; Momose, Y.; Sohda, T.; Oi, S.; Ikeda, H.; Hatanaka, C.; Studies on antidiabetic agents. X. Synthesis and biological activities of pioglitazone and related compounds. Chem Pharm Bull 1991, 39, 6, 1440-5. |
| 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) | 14139 | 2-(5-Ethyl-2-pyridinyl)-1-ethanol | 5223-06-3 | C9H13NO | 详情 | 详情 |
| (II) | 62865 | 2-(5-ethyl-2-pyridinyl)ethyl 4-methylbenzenesulfonate | C16H19NO3S | 详情 | 详情 | |
| (III) | 62866 | 2-(5-ethyl-2-pyridinyl)ethyl methanesulfonate | C10H15NO3S | 详情 | 详情 | |
| (IV) | 13433 | 4-Hydroxybenzaldehyde; p-Hydroxybenzaldehyde | 123-08-0 | C7H6O2 | 详情 | 详情 |
| (V) | 14141 | 4-[2-(5-Ethyl-2-pyridinyl)ethoxy]benzaldehyde | C16H17NO2 | 详情 | 详情 | |
| (VI) | 10883 | 1,3-Thiazolane-2,4-dione; 2,4-Thiazolidinedione | 2295-31-0 | C3H3NO2S | 详情 | 详情 |
| (VII) | 14143 | 5-((E)-[4-[2-(5-Ethyl-2-pyridinyl)ethoxy]phenyl]methylidene)-1,3-thiazolane-2,4-dione | 144809-28-9 | C19H18N2O3S | 详情 | 详情 |
| (VIII) | 14144 | 4-Fluorobenzonitrile | 1194-02-1 | C7H4FN | 详情 | 详情 |
| (IX) | 14145 | 4-[2-(5-Ethyl-2-pyridinyl)ethoxy]benzonitrile | C16H16N2O | 详情 | 详情 |