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【结 构 式】

【分子编号】68699

【品名】1(S)-(2,6-dichloro-3-fluorophenyl)ethanol;(S)-1-(2,6-dichloro-3-fluorophenyl)ethanol

【CA登记号】877397-65-4

【 分 子 式 】C8H7Cl2FO

【 分 子 量 】209.047

【元素组成】C 45.96% H 3.37% Cl 33.92% F 9.09% O 7.65%

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:(VIII)

Mitsunobu coupling between 1(S)-(2,6-dichloro-3-fluorophenyl) ethanol (VIII) and 3-hydroxy-2-nitropyridine (IX) in the presence of DIAD and PPh3 affords ether (X), which by subsequent nitro group reduction using iron and HCl in EtOH yields the aminopyridine (XI). Bromination of compound (XI) by treatment with N-bromosuccinimide provides the bromopyridine (I), which is then submitted to palladium-catalyzed coupling with the pyrazolyl boronate (XII) to give adduct (VII). Finally, the N-Boc protecting group is removed by treatment with HCl .

1 Tran-Dube, M., Shen, H., Yamazaki, S. et al. Lead optimization of 2-amino-3-benzyloxy-5-pyrazol-4-yl-pyridine for the discovery of clinical candidate PF-2341066 as potent and highly selective c-Met inhibitor. 235th ACS Natl Meet (April 6-10, New Orleans) 2008, Abst MEDI 105.
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) 68698 5-bromo-3-[1(R)-(2,6-dichloro-3-fluorophenyl)ethyl]-pyridin-2-amine;(R)-5-bromo-3-(1-(2,6-dichloro-3-fluorophenyl)ethoxy)pyridin-2-amine    C13H10BrCl2FN2O 详情 详情
(VII) 68693 (R)-tert-butyl 4-(4-(6-amino-5-(1-(2,6-dichloro-3-fluorophenyl)ethoxy)pyridin-3-yl)-1H-pyrazol-1-yl)piperidine-1-carboxylate   C26H30Cl2FN5O3 详情 详情
(VIII) 68699 1(S)-(2,6-dichloro-3-fluorophenyl)ethanol;(S)-1-(2,6-dichloro-3-fluorophenyl)ethanol 877397-65-4 C8H7Cl2FO 详情 详情
(IX) 26207 2-nitro-3-pyridinol 15128-82-2 C5H4N2O3 详情 详情
(X) 68700 (R)-3-(1-(2,6-dichloro-3-fluorophenyl)ethoxy)-2-nitropyridine   C13H9Cl2FN2O3 详情 详情
(XI) 68701 (R)-3-(1-(2,6-dichloro-3-fluorophenyl)ethoxy)pyridin-2-amine   C13H11Cl2FN2O 详情 详情
(XII) 68702 tert-butyl 4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)piperidine-1-carboxylate   C19H32BN3O4 详情 详情
Extended Information