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【结 构 式】

【分子编号】23281

【品名】2-(5-bromo-2-propoxyphenyl)-4-(4-chlorophenyl)-1-(4-pyridinyl)-1,4-butanedione

【CA登记号】

【 分 子 式 】C24H21BrClNO3

【 分 子 量 】486.79238

【元素组成】C 59.22% H 4.35% Br 16.41% Cl 7.28% N 2.88% O 9.86%

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)

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.

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
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