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【结 构 式】 
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【分子编号】59238 【品名】N-[2-methoxy-5-(trifluoromethoxy)benzyl]-2-phenyl-3-pyridinamine; N-[2-methoxy-5-(trifluoromethoxy)benzyl]-N-(2-phenyl-3-pyridinyl)amine 【CA登记号】 |
【 分 子 式 】C20H17F3N2O2 【 分 子 量 】374.3624696 【元素组成】C 64.17% H 4.58% F 15.22% N 7.48% O 8.55% |
合成路线1
该中间体在本合成路线中的序号：(VII)In an alternative procedure, the reductive alkylation of 3-amino-2-chloropyridine (IV) with 2-methoxy-5-trifluoromethoxybenzaldehyde (III) in the presence of NaBH(OAc)3 produced the 3-(benzylamino)pyridine (V). The 2-phenyl pyridine derivative (VII) was then prepared by chloride displacement with phenylmagnesium bromide (VI) in the presence of bis(triphenylphosphino)nickel(II) chloride. Catalytic hydrogenation of pyridine (VII) produced the racemic cis-piperidine, which was finally resolved into the enantiomers by using (S)-mandelic acid.
| 【1】 Rosen, T.J.; Godek, D.M.; Ruggeri, S.G.; Wint, L.T. (Pfizer Inc.); Preparation of substd. piperidines. WO 9311110 . |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (III) | 59236 | 2-methoxy-5-(trifluoromethoxy)benzaldehyde | C9H7F3O3 | 详情 | 详情 | |
| (IV) | 11160 | 2-Chloro-3-pyridinamine; 2-Chloro-3-pyridinylamine; 3-Amino-2-chloropyridine; 2-Chloro-3-aminopyridine | 6298-19-7 | C5H5ClN2 | 详情 | 详情 |
| (V) | 59237 | N-(2-chloro-3-pyridinyl)-N-[2-methoxy-5-(trifluoromethoxy)benzyl]amine; 2-chloro-N-[2-methoxy-5-(trifluoromethoxy)benzyl]-3-pyridinamine | C14H12ClF3N2O2 | 详情 | 详情 | |
| (VI) | 17616 | bromo(phenyl)magnesium; Phenyl Magnesium Bromide | 100-58-3 | C6H5BrMg | 详情 | 详情 |
| (VII) | 59238 | N-[2-methoxy-5-(trifluoromethoxy)benzyl]-2-phenyl-3-pyridinamine; N-[2-methoxy-5-(trifluoromethoxy)benzyl]-N-(2-phenyl-3-pyridinyl)amine | C20H17F3N2O2 | 详情 | 详情 |