• English
  • 简体中文
Login Register
Current Location: Home > Feedback Help Print

【结 构 式】

【分子编号】60372

【品名】(6-chloro-3-pyridinyl)methanol

【CA登记号】

【 分 子 式 】C6H6ClNO

【 分 子 量 】143.57248

【元素组成】C 50.19% H 4.21% Cl 24.69% N 9.76% O 11.14%

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)

6-Chloronicotinic acid (I) is converted to the corresponding acid chloride (II) employing either SOCl2 or PCl5/POCl3. Treatment of acid chloride (II) with EtOH and Et3N, followed by reduction of the resultant ethyl ester with LiAlH4, furnishes 6-chloro-3-pyridylmethanol (III). Alcohol (III) is alternatively prepared by NaBH4 reduction of acid chloride (II). Chlorination of (III) by using SOCl2 gives the chloromethyl pyridine (IV), and further chloride displacement with KCN leads to nitrile (V). Substitution of the remaining chloride group of (V) upon heating with pyrrolidine (VI) furnishes the pyrrolidinyl pyridine (VII). Then hydrolysis of the nitrile function of (VII) under acidic conditions provides carboxylic acid (VIII). Bromination of 4-(methylsulfonyl)acetophenone (IX) in the presence of AlCl3 produces the phenacyl bromide (X). Finally, condensation between acid (VIII) and bromo ketone (X) under basic conditions gives rise to the title diaryl furanone

1 Almansa, C.; Alfon, J.; Cavalcanti, F.L.; Gomez, L.; Miralles, A.; Synthesis and SAR of 4-pyrrolidinylarylheterocycles as COX-2 selective inhibitors. Drugs Fut 2002, 27, Suppl. A.
2 Almansa Rosales, C.; Gonzalez Gonzalez, C.; Torres Barreda, M.C. (J. Uriach & Cia., SA); Novel heterocyclic cpds. with anti-inflammatory activity. EP 1281709; ES 2166710; WO 0183475 .
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) 12996 6-Chloronicotinic acid 5326-23-8 C6H4ClNO2 详情 详情
(II) 30256 6-chloronicotinoyl chloride 58757-38-3 C6H3Cl2NO 详情 详情
(III) 60372 (6-chloro-3-pyridinyl)methanol C6H6ClNO 详情 详情
(IV) 60373 2-chloro-5-(chloromethyl)pyridine C6H5Cl2N 详情 详情
(V) 60374 2-(6-chloro-3-pyridinyl)acetonitrile C7H5ClN2 详情 详情
(VI) 11376 Pyrrolidine 123-75-1 C4H9N 详情 详情
(VII) 60375 2-[6-(1-pyrrolidinyl)-3-pyridinyl]acetonitrile C11H13N3 详情 详情
(VIII) 60376 2-[6-(1-pyrrolidinyl)-3-pyridinyl]acetic acid C11H14N2O2 详情 详情
(IX) 19263 1-[4-(methylsulfonyl)phenyl]-1-ethanone; 4-methylsulfonylacetophenone 10297-73-1 C9H10O3S 详情 详情
(X) 19264 2-bromo-1-[4-(methylsulfonyl)phenyl]-1-ethanone C9H9BrO3S 详情 详情
Extended Information