【结 构 式】 |
【分子编号】27744 【品名】4-chloro-8-mesityl-2-methylquinoline 【CA登记号】 |
【 分 子 式 】C19H18ClN 【 分 子 量 】295.81136 【元素组成】C 77.15% H 6.13% Cl 11.98% N 4.74% |
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:(VII)Suzuki coupling of 2-bromoaniline (I) with boronic acid (II) in the presence of a palladium catalyst gave biphenyl (III). Subsequent condensation of (III) with ethyl acetoacetate (IV) afforded enamine (V), which was cyclized to hydroxyquinoline (VI) in refluxing diphenyl ether. Chlorination of (VI) in boiling POCl3 produced the corresponding 4-chloroquinoline (VII). This was finally condensed with N-(cyclopropylmethyl)-N--propylamine (VIII) to provide the target aminoquinoline.
【1】 Huang, C.; Chen, C.; McCarthy, J.R.; Haddach, M.; Wilcoxen, K.M. (Janssen Pharmaceutica NV; Neurocrine Biosciences Inc.); CRF antagonistic quino- and quinazolines. EP 0977737; WO 9847874 . |
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) | 27739 | 2-bromoaniline | 615-36-1 | C6H6BrN | 详情 | 详情 |
(II) | 27740 | mesitylboronic acid | 5980-97-2 | C9H13BO2 | 详情 | 详情 |
(III) | 27741 | 2',4',6'-trimethyl[1,1'-biphenyl]-2-amine | C15H17N | 详情 | 详情 | |
(IV) | 11819 | ethyl acetoacetate; ethyl 3-oxobutanoate;Acetoacetic ester;Ethyl beta-ketobutyrate;ethyl 3-oxobutyrate | 141-97-9 | C6H10O3 | 详情 | 详情 |
(V) | 27742 | ethyl (E)-3-(2-mesitylanilino)-2-butenoate | C21H25NO2 | 详情 | 详情 | |
(VI) | 27743 | 8-mesityl-2-methyl-4-quinolinol | C19H19NO | 详情 | 详情 | |
(VII) | 27744 | 4-chloro-8-mesityl-2-methylquinoline | C19H18ClN | 详情 | 详情 | |
(VIII) | 27745 | N-(cyclopropylmethyl)-1-propanamine | 26389-60-6 | C7H15N | 详情 | 详情 |
Extended Information