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【结 构 式】

【分子编号】12029

【品名】3-Pyridinyl[3-(trifluoromethyl)phenyl]methanol

【CA登记号】

【 分 子 式 】C13H10F3NO

【 分 子 量 】253.2237496

【元素组成】C 61.66% H 3.98% F 22.51% N 5.53% O 6.32%

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:(III)

Grignard reaction of 3-trifluoromethylbenzene-magnesium bromide (II) with 3-pyridinecarboxaldehyde (I) in THF at 15 C gives alpha-[3-(trifluoromethyl)phenyl]-3-pyridinemethanol (III). Oxidation of this compound with MnO2 in refluxing CH2Cl2 yields the corresponding ketone (IV). The oximation reaction carried out with NH2OH.HCl in isopropanol-HCl at 70 C affords (3-pyridinyl)-[3-(trifluoromethyl)phenyl]methanone oxime (V) (more than 90% of the E-isomer). The alkylation of (V) with ethyl bromovalerate in the presence of NaOH in DMF produces ethyl 5-[[[(3-pyridinyl)[3-(trifluoromethyl)phenyl]methylene]amino]oxy] pentanoate (VI). Hydrolysis of the ester with aqueous NaOH followed by HCl treatment gives, after recrystallization from diisopropylether, ridogrel.

1 Freyne, E.J.E.; Raeymaekers, A.H.; Sipido, V.; Venet, M.G. (Janssen Pharmaceutica NV); Pharmaceutical use of [[[(3-pyridinyl)methylen]amino]oxy]alkanoic acid and esters. EP 0221601; JP 1987161759; JP 1991068556; US 4746671 .
2 Freyne, E.J.; Raeymaekers, A.H.M.; Venet, M.G.; Sipido, V.K.; De Clerck, F.; RIDOGREL. Drugs Fut 1990, 15, 5, 463.
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) 12849 Nicotinaldehyde; 3-Pyridinecarboxaldehyde 500-22-1 C6H5NO 详情 详情
(II) 12028 Bromo[3-(trifluoromethyl)phenyl]magnesium 402-26-6 C7H4BrF3Mg 详情 详情
(III) 12029 3-Pyridinyl[3-(trifluoromethyl)phenyl]methanol C13H10F3NO 详情 详情
(IV) 12030 3-Pyridinyl[3-(trifluoromethyl)phenyl]methanone C13H8F3NO 详情 详情
(V) 12031 3-Pyridinyl[3-(trifluoromethyl)phenyl]methanone oxime C13H9F3N2O 详情 详情
Extended Information