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【结 构 式】 
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【分子编号】24382 【品名】6-(2-furyl)-2-pyridinecarbaldehyde 【CA登记号】 |
【 分 子 式 】C10H7NO2 【 分 子 量 】173.17112 【元素组成】C 69.36% H 4.07% N 8.09% O 18.48% |
合成路线1
该中间体在本合成路线中的序号：(X)Acylation of 4-piperidone ethylene ketal (I) with 3-chloro-4-fluorobenzoyl chloride (II) in the presence of Et3N gave amide (III). After ketal hydrolysis of (III) using 80% formic acid and CuSO4, treatment of the resulting N-acyl piperidone (IV) with dimethyloxosulfonium methylide provided epoxide (V). Subsequent ring opening of (V) with HF-pyridine complex afforded the fluoro alcohol (VI), which was converted to tosylate (VII). Then, Gabriel synthesis via the corresponding phthalimide (VIII) produced amine (IX). The title compound was then obtained by condensation of 6-(2-furanyl)pyridine-2-carboxaldehyde (X) with amine (IX), followed by reduction of the intermediate imine with KBH4 in MeOH.
| 【1】 Koek, W.; Cosi, C.; Jubault, N.; Funes, P.; Assié, M.-B.; Vacher, B.; Kleven, M.; Bonnaud, B.; Novel derivatives of 2-pyridinemethylamine as selective, potent, and orally active agonists at 5-HT1A receptors. J Med Chem 1999, 42, 9, 1648. |
| 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) | 11338 | 1,4-Dioxa-8-azaspiro[4.5]decane; 4-Piperidone ethylene ketal | 177-11-7 | C7H13NO2 | 详情 | 详情 |
| (II) | 24370 | 3-chloro-4-fluorobenzoyl chloride | 65055-17-6 | C7H3Cl2FO | 详情 | 详情 |
| (III) | 24371 | (3-chloro-4-fluorophenyl)(1,4-dioxa-8-azaspiro[4.5]dec-8-yl)methanone | C14H15ClFNO3 | 详情 | 详情 | |
| (IV) | 24372 | 1-(3-chloro-4-fluorobenzoyl)-4-piperidinone | C12H11ClFNO2 | 详情 | 详情 | |
| (V) | 24373 | (3-chloro-4-fluorophenyl)(1-oxa-6-azaspiro[2.5]oct-6-yl)methanone | C13H13ClFNO2 | 详情 | 详情 | |
| (VI) | 24374 | (3-chloro-4-fluorophenyl)[4-fluoro-4-(hydroxymethyl)-1-piperidinyl]methanone | C13H14ClF2NO2 | 详情 | 详情 | |
| (VII) | 24375 | [1-(3-chloro-4-fluorobenzoyl)-4-fluoro-4-piperidinyl]methyl 4-methylbenzenesulfonate | C20H20ClF2NO4S | 详情 | 详情 | |
| (VIII) | 24376 | 2-[[1-(3-chloro-4-fluorobenzoyl)-4-fluoro-4-piperidinyl]methyl]-1H-isoindole-1,3(2H)-dione | C21H17ClF2N2O3 | 详情 | 详情 | |
| (IX) | 27377 | 2-chloro-N-cyclohexylacetamide | C8H14ClNO | 详情 | 详情 | |
| (X) | 24382 | 6-(2-furyl)-2-pyridinecarbaldehyde | C10H7NO2 | 详情 | 详情 |