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【结 构 式】 
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【分子编号】58667 【品名】2-fluoro-4-hydrazinobenzonitrile 【CA登记号】 |
【 分 子 式 】C7H6FN3 【 分 子 量 】151.1432632 【元素组成】C 55.63% H 4% F 12.57% N 27.8% |
合成路线1
该中间体在本合成路线中的序号：(I)The intermediate aldehyde (VII) has been obtained as follows: The cyclization of 2-fluoro-4-hydrazinobenzonitrile (I) with malonaldehyde (II) by means of HCl in refluxing ethanol gives 2-fluoro-4-(1-pyrazolyl)benzonitrile (III), which is reduced by means of diisobutylaluminum hydride in toluene to yield the benzaldehyde (IV). The condensation of (IV) with (1,3-dioxolan-2-ylmethyl)triphenylphosphonium bromide (V) by means of TDA-1 and K2CO3 in refluxing dichloromethane to afford the 3-[2-fluoro-4-(1-pyrazolyl)phenyl]-2-propenal ethylene ketal (VI), which is finally hydrolyzed with HCl in THF to provide the target intermediate aldehyde (VII).
| 【1】 Henninger, T.C.; Xu, X.C. (Ortho-McNeil Pharmaceutical, Inc.); 6-O-Carbamoyl ketolide derivs. of erythromycin useful as antibacterials. US 6472372; WO 0246204 . |
| 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) | 58667 | 2-fluoro-4-hydrazinobenzonitrile | C7H6FN3 | 详情 | 详情 | |
| (II) | 58668 | 1,1,3,3-Tetramethoxypropane; Malonaldehyde bis(dimethylacetal); Malonaldehyde tetramethylacetal | 102-52-3 | C7H16O4 | 详情 | 详情 |
| (III) | 58669 | 2-fluoro-4-(1H-pyrazol-1-yl)benzonitrile | C10H6FN3 | 详情 | 详情 | |
| (IV) | 58670 | 2-fluoro-4-(1H-pyrazol-1-yl)benzaldehyde | C10H7FN2O | 详情 | 详情 | |
| (V) | 18641 | (1,3-dioxolan-2-ylmethyl)(triphenyl)phosphonium bromide | 52509-14-5 | C22H22BrO2P | 详情 | 详情 |
| (VI) | 58671 | 1-{4-[(E)-2-(1,3-dioxolan-2-yl)ethenyl]-3-fluorophenyl}-1H-pyrazole | C14H13FN2O2 | 详情 | 详情 | |
| (VII) | 58672 | (E)-3-[2-fluoro-4-(1H-pyrazol-1-yl)phenyl]-2-propenal | C12H9FN2O | 详情 | 详情 |