isopropyl 2-cyanoacetate -Drug Synthesis Database

【结构式】

【分子编号】63543

【品名】isopropyl 2-cyanoacetate

【CA登记号】

【分子式】C₆H₉NO₂

【分子量】127.143

【元素组成】C 56.68% H 7.13% N 11.02% O 25.17%

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：(IV)

5-Fluoroisatin (I) is alkylated with 4-methylbenzyl bromide (II) in the presence of NaH to afford the N-benzyl isatin derivative (III). Then, Knoevenagel condensation of isatin (III) with isopropyl cyanoacetate (IV) by means of piperidine in isopropanol gives the indolinylidene adduct (V) as a mixture of E and Z isomers. Subsequent catalytic hydrogenation of (V) over Pd/C then furnishes the target compound

参考文献中间体

合成目标

【1】 Da Settimo, F.; Primofiore, G.; Da Settimo, A.; La Motta, C.; Simorini, F.; Novellino, E.; Greco, G.; Lavecchia, A.; Boldrini, E.; Novel, highly potent aldose reductase inhibitors: Cyano(2-oxo-2,3-dihydroindol-3-yl)acetic acid derivatives. J Med Chem 2003, 46, 8, 1419.

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)	21552	5-fluoro-1H-indole-2,3-dione	443-69-6	C₈H₄FNO₂	详情	详情
(II)	24623	1-(bromomethyl)-4-methylbenzene	104-81-4	C₈H₉Br	详情	详情
(III)	63541	5-fluoro-1-(4-methylbenzyl)-1H-indole-2,3-dione		C₁₆H₁₂FNO₂	详情	详情
(IV)	63543	isopropyl 2-cyanoacetate		C₆H₉NO₂	详情	详情
(V)	63544	isopropyl 2-cyano-2-[5-fluoro-1-(4-methylbenzyl)-2-oxo-1,2-dihydro-3H-indol-3-ylidene]acetate		C₂₂H₁₉FN₂O₃	详情	详情

Extended Information