(4-fluorophenyl)(1H-indol-5-yl)methanone -Drug Synthesis Database

【结构式】

【分子编号】29515

【品名】(4-fluorophenyl)(1H-indol-5-yl)methanone

【CA登记号】

【分子式】C₁₅H₁₀FNO

【分子量】239.2489432

【元素组成】C 75.3% H 4.21% F 7.94% N 5.85% O 6.69%

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)

The reaction of 4-fluorobenzoyl chloride (I) with N,O-dimethylhydroxylamine (II) in pyridine gives the N-methylhydroxamate (III), which is condensed with 5-bromo-1H-indole (IV) by means of KH and t-BuLi yielding the ketone (V). The alkylation of (V) with ethyl iodide and NaH in DMF affords (1-ethylindol-5-yl)(4-fluorophenyl)methanone (VI), which is reduced with NaBH4 in methanol to the corresponding carbinol (VII). Finally, this compound is treated with carbonyl diimidazole in THF.

参考文献中间体

合成目标

【1】 Marchand, P.; Robert, J.-M.; Palzer, M.; Delovoye-Seiller, B.; Hartmann, R.W.; Le Baut, G.; Le Borgne, M.; New selective nonsteroidal aromatase inhibitors: Synthesis and inhibitory activity of 2, 3 or 5-(alpha-azolylbenzyl)-1H-indoles. Bioorg Med Chem Lett 1999, 9, 3, 333.

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)	17263	4-fluorobenzoyl chloride	403-43-0	C₇H₄ClFO	详情	详情
(II)	13361	(Methoxyamino)methane; N,O-Dimethylhydroxylamine	1117-97-1	C₂H₇NO	详情	详情
(III)	29514	4-fluoro-N-methoxy-N-methylbenzamide		C₉H₁₀FNO₂	详情	详情
(IV)	13309	5-Bromo-1H-indole; 5-Bromoindole	10075-50-0	C₈H₆BrN	详情	详情
(V)	29515	(4-fluorophenyl)(1H-indol-5-yl)methanone		C₁₅H₁₀FNO	详情	详情
(VI)	29516	(1-ethyl-1H-indol-5-yl)(4-fluorophenyl)methanone		C₁₇H₁₄FNO	详情	详情
(VII)	29517	(1-ethyl-1H-indol-5-yl)(4-fluorophenyl)methanol		C₁₇H₁₆FNO	详情	详情
(VIII)	11353	1,1'-Carbonyldiimidazole; Di(1H-imidazol-1-yl)methanone; N,N-Carbonyldiimidazole; 1,1'-Carbonylbis(1H-imidazole)	530-62-1	C₇H₆N₄O	详情	详情

Extended Information