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【结 构 式】 
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【分子编号】68648 【品名】tert-butyl 3-(3-methylpyridin-2-yl)benzoate 【CA登记号】 |
【 分 子 式 】C17H19NO2 【 分 子 量 】269.3434 【元素组成】C 75.81% H 7.11% N 5.2% O 11.88% |
与该中间体有关的原料药合成路线共 1 条
合成路线1
该中间体在本合成路线中的序号：(XXIV)Intermediate (XVI) is prepared by Suzuki coupling of 2-bromo-3-methylpyridine (XXII) with 3-(tert-butoxycarbonyl)phenylboronic acid (XXIII) in the presence of PdCl2(dppf) and K2CO3 in toluene at 65 °C to give tert-butyl 3-(3-methylpyridin-2-yl)benzoate (XXIV), which upon oxidation of the pyridine ring using urea-hydrogen peroxide and phthalic anhydride in EtOAc/H2O furnishes the pyridine-N-oxide (XXV). Finally, compound (XXV) is submited to rearrangement with Ms2O in the presence of pyridine in acetonitrile at 70 °C followed by quenching with ethanolamine .
| 【1】 Siesel, D. (Vertex Pharmaceuticals, Inc.). Processes for producing cycloalkylcarboxamido-pyridine benzoic acids. CN 101910134, EP 2231606, JP 2011506332, KR 201010132, US 2009176989, US 8124781, US 2012190856, WO 2009076142. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (XVI) | 68642 | tert-butyl 3-(6-amino-3-methylpyridin-2-yl)benzoate | C17H20N2O2 | 详情 | 详情 | |
| (XXII) | 57602 | 2-Bromo-3-methylpyridine; 2-Bromo-3-picoline | 3430-17-9 | C6H6BrN | 详情 | 详情 |
| (XXIII) | 68646 | 3-(tert-butoxycarbonyl)phenylboronic acid;3-tert-Butoxycarbonylphenylboronic acid | 220210-56-0 | C11H15BO4 | 详情 | 详情 |
| (XXIV) | 68648 | tert-butyl 3-(3-methylpyridin-2-yl)benzoate | C17H19NO2 | 详情 | 详情 | |
| (XXV) | 68647 | 2-(3-(tert-butoxycarbonyl)phenyl)-3-methylpyridine 1-oxide | C17H19NO3 | 详情 | 详情 |
Extended Information