3-bromo-5-(2-oxiranyl)isoxazole -Drug Synthesis Database

【结构式】

【分子编号】22870

【品名】3-bromo-5-(2-oxiranyl)isoxazole

【CA登记号】

【分子式】C₅H₄BrNO₂

【分子量】189.9963

【元素组成】C 31.61% H 2.12% Br 42.06% N 7.37% O 16.84%

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：(VII)

The condensation of 3-bromo-5-isoxazolylcarbonyl chloride (I) with diethyl malonate (II) gives the corresponding malonyl derivative (III), which is submitted to a decarboxylative hydrolysis yielding 5-acetyl-3-bromoisoxazole (IV). Bromination of (IV) affords 5-(bromoacetyl)-3-bromoisoxazole (V), which is reduced to 2-bromo-1-(3-bromo-5-isoxazolyl)ethanol (VI). Title compound is obtained by reaction of (VI) with tert-butylamine directly or via oxirane (VII), which is obtained by reaction of (VI) with sodium hydride, and finally by reaction of (VII) with tert-butylamine.

参考文献中间体

合成目标

【1】 Fantucci, M.; Sala, R.; Chiarino, D.; Frigeni, V.; Della Bella, D.; Carenzi, A.; New isoxazole derivatives with a potent and select. Farm Sci Ed 1986, 41, 6, 440.
【2】 Chiarino, D.; Della Bella, D. (Zambon Group SpA); 1-(3-Bromo-isoxazol-5-yl)-2-tert-butylaminoethanol. JP 1980108862; US 4276299 .
【3】 Castaner, J.; Prous, J.; Broxaterol. Drugs Fut 1987, 12, 2, 107.

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)	22864	3-bromo-5-isoxazolecarbonyl chloride		C₄HBrClNO₂	详情	详情
(II)	16829	Diethyl malonate	105-53-3	C₇H₁₂O₄	详情	详情
(III)	22866	diethyl 2-[(3-bromo-5-isoxazolyl)carbonyl]malonate		C₁₁H₁₂BrNO₆	详情	详情
(IV)	22867	1-(3-bromo-5-isoxazolyl)-1-ethanone		C₅H₄BrNO₂	详情	详情
(V)	22868	2-bromo-1-(3-bromo-5-isoxazolyl)-1-ethanone		C₅H₃Br₂NO₂	详情	详情
(VI)	22869	2-bromo-1-(3-bromo-5-isoxazolyl)-1-ethanol		C₅H₅Br₂NO₂	详情	详情
(VII)	22870	3-bromo-5-(2-oxiranyl)isoxazole		C₅H₄BrNO₂	详情	详情

Extended Information