4-[(5-fluoro-1H-inden-2-yl)methyl]-4,5-dihydro-1H-imidazole -Drug Synthesis Database

【结构式】

【分子编号】46424

【品名】4-[(5-fluoro-1H-inden-2-yl)methyl]-4,5-dihydro-1H-imidazole

【CA登记号】

【分子式】C₁₃H₁₃FN₂

【分子量】216.2581032

【元素组成】C 72.2% H 6.06% F 8.79% N 12.95%

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：(XI)

In an alternative procedure, Wadsworth-Emmons condensation of 5-fluoroindan-2-one (VI) with triethyl phosphonoacetate gave the indeneacetate (VII), which was reduced to aldehyde (VIII) employing diisobutylaluminum hydride. Strecker reaction of aldehyde (VIII) with NaCN and NH-4-Cl produced amino nitrile (IX). This was reduced to diamine (X) using LiAlH4, and then condensed with formamidine acetate to produce imidazoline (XI). Finally, catalytic hydrogenation of indene (XI) over Pd/C provided the title indane derivative.

参考文献中间体

合成目标

【1】 Persigand, T.; Lacoste, J.-M.; Audinot, V.; Millan, M.J.; Newman-Tancredi, A.; Cordi, A.A.; Berque-Bestel, I.; Potential antidepressants displayed combined alpha2-adrenoceptor antagonist and monoamine uptake inhibitor properties. J Med Chem 2001, 44, 5, 787.

中间体序号	中间体编号	品名	分子式	供应商	用于合成
(VI)	46419	5-fluoro-1,3-dihydro-2H-inden-2-one	C₉H₇FO	详情	详情
(VII)	46420	ethyl 2-(5-fluoro-1H-inden-2-yl)acetate	C₁₃H₁₃FO₂	详情	详情
(VIII)	46421	2-(5-fluoro-1H-inden-2-yl)acetaldehyde	C₁₁H₉FO	详情	详情
(IX)	46422	2-amino-3-(5-fluoro-1H-inden-2-yl)propanenitrile	C₁₂H₁₁FN₂	详情	详情
(X)	46423	3-(5-fluoro-1H-inden-2-yl)-1,2-propanediamine; 2-amino-1-[(5-fluoro-1H-inden-2-yl)methyl]ethylamine	C₁₂H₁₅FN₂	详情	详情
(XI)	46424	4-[(5-fluoro-1H-inden-2-yl)methyl]-4,5-dihydro-1H-imidazole	C₁₃H₁₃FN₂	详情	详情

Extended Information