3-(3-fluorophenyl)propanal -Drug Synthesis Database

【结构式】

【分子编号】25651

【品名】3-(3-fluorophenyl)propanal

【CA登记号】

【分子式】C₉H₉FO

【分子量】152.1682632

【元素组成】C 71.04% H 5.96% F 12.49% O 10.51%

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：(IX)

Alkylation of N-Boc-piperazine (I) with bromoacetal (II) provided piperazine acetal (III). This was submitted to Fisher cyclization with 4-(1,2,4-triazol-4-yl)phenyl hydrazine (IV) in aqueous H2SO4 to afford the deprotected indole (V). Wittig reaction of 3-fluorobenzaldehyde (VII) with phosphorane prepared from (methoxymethyl)phosphonium salt (VI) and PhLi furnished the methoxyvinyl compound (VIII) as an E:Z mixture. Subsequent acid hydrolysis of the enol ether function of (VIII) yielded aldehyde (IX). The target compound was then obtained by reductive alkylation of piperazine (V) with aldehyde (IX) in the presence of NaBH3CN.

参考文献中间体

合成目标

【1】 Chambers, M.S.; Goodacre, S.; Street, L.J.; et al.; 3-(Piperazinylpropyl)indoles: Selective, orally bioavailable h5-HT1D receptor agonists as potential antimigraine agents. J Med Chem 1999, 42, 4, 691.

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(VIIIa)	25650	1-fluoro-3-[(E)-2-methoxyethenyl]benzene; (E)-2-(3-fluorophenyl)ethenyl methyl ether		C₉H₉FO	详情	详情
(VIIIb)	53875	(Z)-2-(3-fluorophenyl)ethenyl methyl ether; 1-fluoro-3-[(Z)-2-methoxyethenyl]benzene	n/a	C₉H₉FO	详情	详情
(I)	13225	N-tert-Butoxycarbonyl piperazine; tert-butyl 1-piperazinecarboxylate;tert-butyl piperazine-1-carboxylate	143238-38-4	C₉H₁₈N₂O₂	详情	详情
(II)	25645	5-bromo-1-methoxypentyl methyl ether; 5-bromo-1,1-dimethoxypentane		C₇H₁₅BrO₂	详情	详情
(III)	25646	tert-butyl 4-(5,5-dimethoxypentyl)-1-piperazinecarboxylate		C₁₆H₃₂N₂O₄	详情	详情
(IV)	25647	4-(4-hydrazinophenyl)-4H-1,2,4-triazole		C₈H₉N₅	详情	详情
(V)	25648	3-[3-(1-piperazinyl)propyl]-5-(4H-1,2,4-triazol-4-yl)-1H-indole		C₁₇H₂₂N₆	详情	详情
(VI)	25649	(methoxymethyl)(triphenyl)phosphonium bromide		C₂₀H₂₀BrOP	详情	详情
(VII)	18887	3-Fluorobenzaldehyde	456-48-4	C₇H₅FO	详情	详情
(IX)	25651	3-(3-fluorophenyl)propanal		C₉H₉FO	详情	详情

Extended Information