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【结 构 式】

【分子编号】44739

【品名】ethyl 3-(3-ethoxy-3-oxopropyl)-4,5,6,7-tetrahydro-1H-indole-2-carboxylate

【CA登记号】

【 分 子 式 】C16H23NO4

【 分 子 量 】293.36296

【元素组成】C 65.51% H 7.9% N 4.77% O 21.82%

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:(V)

Condensation of ethyl succinyl chloride (II) with 4-(1-cyclohexenyl)morpholine (I) in the presence of Et3N produced enamino ketoester (III). Cyclization of (III) with diethyl aminomalonate (IV) gave the tetrahydroindole (V). Hydrolysis of the ester functions of (V) with NaOH, followed by acidic decarboxylation, afforded the tetrahydroindolylpropionic acid (VI). Vilsmeier formylation of (VI) with DMF and POCl3 furnished aldehyde (VII). This was then condensed with 5-bromo-2-oxindole (IX) (obtained by treatment of (VIII) with N-bromosuccinimide), using either pyrrolidine or piperidine in refluxing EtOH to yield the title compound.

2 Miller, T.A.; Tang, P.C.; Sun, L.; Tran, N.M.; Liang, C.; Nguyen, A.T.; Nematalla, A. (Sugen, Inc.); 3-Methylidenyl-2-indolinone modulators of protein kinase. WO 0008202 .
1 Liang, C.; Sun, L.; Tran, N.; et al.; Identification of substituted 3-[(4,5,6,7-tetrahydro-1H-indol-2-yl)methylene]-1,3-dihydroindol-2-ones as growth factor receptor inhibitors for VEGF-R2 (F1k-1/KDR), FGF-R1, and PDGF-Rbeta tyrosine kinases. J Med Chem 2000, 43, 14, 2655.
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) 44735 4-(1-cyclohexen-1-yl)morpholine 670-80-4 C10H17NO 详情 详情
(II) 40684 ethyl 4-chloro-4-oxobutanoate; Ethyl succinyl chloride 14794-31-1 C6H9ClO3 详情 详情
(III) 44737 ethyl 4-[2-(4-morpholinyl)-1-cyclohexen-1-yl]-4-oxobutanoate C16H25NO4 详情 详情
(IV) 44738 Diethyl aminomalonate; diethyl 2-aminomalonate C7H13NO4 详情 详情
(V) 44739 ethyl 3-(3-ethoxy-3-oxopropyl)-4,5,6,7-tetrahydro-1H-indole-2-carboxylate C16H23NO4 详情 详情
(VI) 44740 3-(4,5,6,7-tetrahydro-1H-indol-3-yl)propionic acid C11H15NO2 详情 详情
(VII) 44741 3-(2-formyl-4,5,6,7-tetrahydro-1H-indol-3-yl)propionic acid C12H15NO3 详情 详情
(VIII) 18699 1,3-dihydro-2H-indol-2-one 59-48-3 C8H7NO 详情 详情
(IX) 44743 5-bromo-1,3-dihydro-2H-indol-2-one C8H6BrNO 详情 详情
Extended Information