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【结 构 式】

【分子编号】35748

【品名】3-[4-(methylsulfonyl)phenyl]-5-(trifluoromethyl)-2(1H)-pyridinone

【CA登记号】

【 分 子 式 】C13H10F3NO3S

【 分 子 量 】317.2885496

【元素组成】C 49.21% H 3.18% F 17.96% N 4.41% O 15.13% S 10.11%

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:(X)

Bromination of 2-amino-5-trifluoromethylpyridine (V) in AcOH provided bromopyridine (VI), which was submitted to a Suzuki coupling with 4-(methylthio)benzeneboronic acid (VII) yielding the phenylpyridine derivative (VIII). Oxidation of the methylthio group of (VIII) to the corresponding sulfone (IX) was carried out by treatment with N-methylmorpholine-N-oxide in the presence of OsO4. Diazotization of the amino group of (IX) generated the pyridone (X), and further chlorination employing POCl3 provided chloropyridine (XI). Finally, condensation of (XI) with (S)-2-mercaptopropanol (IV) yielded the title compound.

1 Friesen, R.W.; Deschênes, D.; Gordon, R.; Brideau, C.; Riendau, D.; Savoie, C.; Dubé, D.; Girard, Y.; Fortin, R.; Chan, C.-C.; 2-Heterosubstituted-3-(4-methylsulfonyl)phenyl-5-trifluromethyl pyridines as selective and orally active cyclooxygenase-2 inhibitors. Bioorg Med Chem Lett 1999, 9, 12, 1715.
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) 35743 (2S)-2-sulfanyl-1-propanol C3H8OS 详情 详情
(V) 35744 5-(trifluoromethyl)-2-pyridinylamine; 5-(trifluoromethyl)-2-pyridinamine 74784-70-6 C6H5F3N2 详情 详情
(VI) 35745 3-bromo-5-(trifluoromethyl)-2-pyridinamine; 3-bromo-5-(trifluoromethyl)-2-pyridinylamine C6H4BrF3N2 详情 详情
(VII) 18561 4-(methylsulfanyl)phenylboronic acid 98546-51-1 C7H9BO2S 详情 详情
(VIII) 35746 3-[4-(methylsulfanyl)phenyl]-5-(trifluoromethyl)-2-pyridinamine; 3-[4-(methylsulfanyl)phenyl]-5-(trifluoromethyl)-2-pyridinylamine C13H11F3N2S 详情 详情
(IX) 35747 3-[4-(methylsulfonyl)phenyl]-5-(trifluoromethyl)-2-pyridinylamine; 3-[4-(methylsulfonyl)phenyl]-5-(trifluoromethyl)-2-pyridinamine C13H11F3N2O2S 详情 详情
(X) 35748 3-[4-(methylsulfonyl)phenyl]-5-(trifluoromethyl)-2(1H)-pyridinone C13H10F3NO3S 详情 详情
(XI) 35749 2-chloro-3-[4-(methylsulfonyl)phenyl]-5-(trifluoromethyl)pyridine; 4-[2-chloro-5-(trifluoromethyl)-3-pyridinyl]phenyl methyl sulfone C13H9ClF3NO2S 详情 详情
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