3-(1,4-dioxaspiro[4.5]dec-8-yl)-1H-indole-5-carbonitrile -Drug Synthesis Database

【结构式】

【分子编号】52019

【品名】3-(1,4-dioxaspiro[4.5]dec-8-yl)-1H-indole-5-carbonitrile

【CA登记号】

【分子式】C₁₇H₁₈N₂O₂

【分子量】282.3422

【元素组成】C 72.32% H 6.43% N 9.92% O 11.33%

与该中间体有关的原料药合成路线共 2 条

合成路线1 合成路线2

合成路线1

该中间体在本合成路线中的序号：(IX)

The intermediate 4-(5-cyano-1H-indol-3-yl)cyclohexanone (V) has been obtained as follows: The condensation of 1H-indole-5-carbonitrile (VI) with cyclohexanone monoethyleneketal (VII) by means of KOH in refluxing methanol gives the cyclohexenone ethyleneketal (VIII), which is reduced with H2 over Pd/C in ethanol to yield 4-(5-cyano-1H-indol-3-yl)cyclohexanone ethyleneketal (IX). Finally, this compound is hydrolyzed to the target intermediate (V) with HCl in THF.

参考文献中间体

合成目标

【1】 Meagher, K.L.; et al.; Studies towards the next generation of antidepressants. Part 1: Indolylcyclohexylamines as potent serotonin reuptake inhibitors. Bioorg Med Chem Lett 2001, 11, 14, 1885.
【2】 Meagher, K.L.; Smith, D.L.; Scerni, R.; Shi, X.; Albuthawa, S.; Andree, T.H.; Mewshaw, R.E.; Schechter, L.E.; Evrard, D.A.; Indolylcyclohexylamines as potent serotonin reuptake inhibitors. 219th ACS Natl Meet (March 26 2000, San Francisco) 2000, Abst MEDI 108.

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(V)	47079	3-(4-oxocyclohexyl)-1H-indole-5-carbonitrile		C₁₅H₁₄N₂O	详情	详情
(VI)	31341	5-Cyanoindole; Indole-5-carbonitrile; 1H-Indole-5-carbonitrile	15861-24-2	C₉H₆N₂	详情	详情
(VII)	11377	1,4-Dioxaspiro[4.5]decan-8-one	4746-97-8	C₈H₁₂O₃	详情	详情
(VIII)	52018	3-(1,4-dioxaspiro[4.5]dec-7-en-8-yl)-1H-indole-5-carbonitrile		C₁₇H₁₆N₂O₂	详情	详情
(IX)	52019	3-(1,4-dioxaspiro[4.5]dec-8-yl)-1H-indole-5-carbonitrile		C₁₇H₁₈N₂O₂	详情	详情

合成路线2

该中间体在本合成路线中的序号：(IV)

Base-catalyzed condensation of 5-cyanoindole (I) with 1,4-cyclohexanedione mono-ethylene ketal (II) furnished the cyclohexenyl indole (III), which was further hydrogenated in the presence of Pd/C to the cyclohexyl analogue (IV). Subsequent hydrolysis of the ethylene ketal function of (IV) gave ketone (V).

参考文献中间体

合成目标

【1】 Meagher, K.L.; et al.; Studies towards the next generation of antidepressants. Part 1: Indolylcyclohexylamines as potent serotonin reuptake inhibitors. Bioorg Med Chem Lett 2001, 11, 14, 1885.

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)	31341	5-Cyanoindole; Indole-5-carbonitrile; 1H-Indole-5-carbonitrile	15861-24-2	C₉H₆N₂	详情	详情
(II)	11377	1,4-Dioxaspiro[4.5]decan-8-one	4746-97-8	C₈H₁₂O₃	详情	详情
(III)	52018	3-(1,4-dioxaspiro[4.5]dec-7-en-8-yl)-1H-indole-5-carbonitrile		C₁₇H₁₆N₂O₂	详情	详情
(IV)	52019	3-(1,4-dioxaspiro[4.5]dec-8-yl)-1H-indole-5-carbonitrile		C₁₇H₁₈N₂O₂	详情	详情
(V)	47079	3-(4-oxocyclohexyl)-1H-indole-5-carbonitrile		C₁₅H₁₄N₂O	详情	详情

Extended Information