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【结 构 式】 
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【分子编号】63243 【品名】2-chloro-1-iodo-4-(trifluoromethoxy)benzene; 3-chloro-4-iodophenyl trifluoromethyl ether 【CA登记号】 |
【 分 子 式 】C7H3ClF3IO 【 分 子 量 】322.4525996 【元素组成】C 26.07% H 0.94% Cl 10.99% F 17.68% I 39.36% O 4.96% |
合成路线1
该中间体在本合成路线中的序号：(VII)Chlorination of 4-(trifluoromethoxy)aniline (V) employing N-chlorosuccinimide affords the 2-chloro aniline (VI). Diazotization of aniline (VI) and subsequent quenching with potassium iodide gives rise to the aryl iodide (VII). This is converted into the arylboronic acid (VIII) by lithiation with butyllithium, followed by reaction with triisopropyl borate. Suzuki coupling between chloropyridine (IV) and boronic acid (VIII) leads to the phenylpyridine (IX). Reduction of the nitro group of (IX) employing sodium dithionite provides the diaminopyridine (X). This is finally condensed with triethyl orthopropionate to produce the target imidazopyridine compound.
| 【1】 Arvanitis, A.G.; Rescinito, J.T.; Arnold, C.R.; Wilde, R.G.; Fitzgerald, L.W.; Zaczek, R.; Hartig, P.R.; Grossman, S.; Arneric, S.P.; Gilligan, P.J.; Olson, R.E.; Robertson, D.W.; Imidazo[4,5-c]pyridines as corticotropin releasing factor receptor ligands. Bioorg Med Chem Lett 2003, 13, 1, 129. |
| 【2】 Wilde, R.G.; Bakthavatchalam, R.; Beck, J.P.; Arvanitis, A. (Bristol-Myers Squibb Co.); Imidazopyrimidinyl and imidazopyridinyl derivs.. EP 1244666; JP 2003516992; WO 0144248 . |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (IV) | 63241 | N-(2-chloro-3-nitro-4-pyridinyl)-N-[(1S)-1-methylbutyl]amine; 2-chloro-N-[(1S)-1-methylbutyl]-3-nitro-4-pyridinamine | C10H14ClN3O2 | 详情 | 详情 | |
| (V) | 11131 | 4-(Trifluoromethoxy)aniline; 4-(Trifluoromethoxy)phenylamine | 461-82-5 | C7H6F3NO | 详情 | 详情 |
| (VI) | 63242 | 2-chloro-4-(trifluoromethoxy)aniline; 2-chloro-4-(trifluoromethoxy)phenylamine | C7H5ClF3NO | 详情 | 详情 | |
| (VII) | 63243 | 2-chloro-1-iodo-4-(trifluoromethoxy)benzene; 3-chloro-4-iodophenyl trifluoromethyl ether | C7H3ClF3IO | 详情 | 详情 | |
| (VIII) | 63244 | 2-chloro-4-(trifluoromethoxy)phenylboronic acid | C7H5BClF3O3 | 详情 | 详情 | |
| (IX) | 63245 | 2-[2-chloro-4-(trifluoromethoxy)phenyl]-N-[(1S)-1-methylbutyl]-3-nitro-4-pyridinamine; N-{2-[2-chloro-4-(trifluoromethoxy)phenyl]-3-nitro-4-pyridinyl}-N-[(1S)-1-methylbutyl]amine | C17H17ClF3N3O3 | 详情 | 详情 | |
| (X) | 63246 | N-{3-amino-2-[2-chloro-4-(trifluoromethoxy)phenyl]-4-pyridinyl}-N-[(1S)-1-methylbutyl]amine; 2-[2-chloro-4-(trifluoromethoxy)phenyl]-N~4~-[(1S)-1-methylbutyl]-3,4-pyridinediamine | C17H19ClF3N3O | 详情 | 详情 |