(E)-3-(5-bromo-2-propoxyphenyl)-1-(4-chlorophenyl)-2-propen-1-one -Drug Synthesis Database

【结构式】

【分子编号】23279

【品名】(E)-3-(5-bromo-2-propoxyphenyl)-1-(4-chlorophenyl)-2-propen-1-one

【CA登记号】

【分子式】C₁₈H₁₆BrClO₂

【分子量】379.68054

【元素组成】C 56.94% H 4.25% Br 21.05% Cl 9.34% O 8.43%

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：(III)

Aldol condensation of 5-bromo-2-propoxybenzaldehyde (I) with 4'-chloroacetophenone in the presence of NaOH produced chalcone (III) (1), which was condensed with pyridine-4-carbaldehyde (IV) using NaCN as the catalyst to yield diketone (V). Finally, the target pyrrole was constructed by Paal-Knorr synthesis using diketone (V) and ammonium acetate in boiling AcOH.

参考文献中间体

合成目标

【1】 Li, B.; Kim, D.; MacCoss, M.; de Laszlo, S.E.; Koch, G.E.; hacker, C.; Mantlo, N.; Pivinichny, J.V.; Cascieri, M.A.; Hagmann, W.K.; The development of 2-pyridyl-3,5-diaryl-pyrroles a. 15th European Federation for Medicinal Chemistry International Symposium on Medicinal Chemistry (Sept 6 1998, Edinburgh) 1998, Abst P.232.
【2】 Li, B.; Hacker, C.; De Laszlo, S.E.; et al.; Potent, orally absorbed glucagon receptor antagonists. Bioorg Med Chem Lett 1999, 9, 5, 641.
【3】 de Laszlo, S.E.; Kim, D.; Chang, L.L.; Mantlo, N.B. (Merck & Co., Inc.); Substd. pyridyl pyrroles, compsns. containing such cpds. and methods of use. US 5776954 .
【4】 De Laszlo, S.E.; Chang, L.L.; Kim, D.; Mantlo, N.B. (Merck & Co., Inc.); Substd. pyridyl pyrroles, compsns. containing such cpds. and methods of use. EP 0859771; JP 1999514651; WO 9716442 .

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)	23277	5-bromo-2-propoxybenzaldehyde		C₁₀H₁₁BrO₂	详情	详情
(II)	12685	4-Chloroacetophenone; 1-(4-Chlorophenyl)-1-ethanone; p-Chloroacetophenone	99-91-2	C₈H₇ClO	详情	详情
(III)	23279	(E)-3-(5-bromo-2-propoxyphenyl)-1-(4-chlorophenyl)-2-propen-1-one		C₁₈H₁₆BrClO₂	详情	详情
(IV)	17203	4-Pyridinecarboxaldehyde; isonicotinaldehyde	872-85-5	C₆H₅NO	详情	详情
(V)	23281	2-(5-bromo-2-propoxyphenyl)-4-(4-chlorophenyl)-1-(4-pyridinyl)-1,4-butanedione		C₂₄H₂₁BrClNO₃	详情	详情

Extended Information