methyl (Z)-2-bromo-3-phenyl-2-propenoate -Drug Synthesis Database

【结构式】

【分子编号】44866

【品名】methyl (Z)-2-bromo-3-phenyl-2-propenoate

【CA登记号】

【分子式】C₁₀H₉BrO₂

【分子量】241.08426

【元素组成】C 49.82% H 3.76% Br 33.14% O 13.27%

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：(XVII)

Intermediate (XIV) can be obtained as follows: Bromination of methyl cinnamate (XV) with Br2 in CH2Cl2 provides 2,3-dibromo-3-phenylpropanoate (XVI), which is then converted into alpha-bromocinnamic ester (XVII) by reaction with Et3N in refluxing toluene. Treatment of (XVII) with imidazopyridine (XVIII) and NaH in DMF affords derivative (XIX), which is then hydrolyzed by treatment with NaOH in MeOH to furnish carboxylic acid (XX). Finally, (XX) reacts with carbonylditriazole in DMF to give the target intermediate (XIV).

参考文献中间体

合成目标

【1】 Hemmerle, H.; Schubert, G.; Burger, H.-J.; Herling, A.; Efendic, S. (Aventis SA); Cyclohexane derivs., processes for their preparation and their use as glucose-6-phosphatase inhibitors. CA 2149007; CA 4416433; EP 0682024; JP 1995330767; US 5739147 .

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(XIV)	44863			C₁₇H₁₂N₆O	详情	详情
(XV)	23888	methyl (E)-3-phenyl-2-propenoate	103-26-4	C₁₀H₁₀O₂	详情	详情
(XVI)	44865	methyl 2,3-dibromo-3-phenylpropanoate		C₁₀H₁₀Br₂O₂	详情	详情
(XVII)	44866	methyl (Z)-2-bromo-3-phenyl-2-propenoate		C₁₀H₉BrO₂	详情	详情
(XVIII)	44867	1H-imidazo[4,5-b]pyridine		C₆H₅N₃	详情	详情
(XIX)	44868	methyl (Z)-3-(1H-imidazo[4,5-b]pyridin-1-yl)-3-phenyl-2-propenoate		C₁₆H₁₃N₃O₂	详情	详情
(XX)	44869	(Z)-3-(1H-imidazo[4,5-b]pyridin-1-yl)-3-phenyl-2-propenoic acid		C₁₅H₁₁N₃O₂	详情	详情
(XXI)	44870	di(1H-1,2,4-triazol-1-yl)methanone		C₅H₄N₆O	详情	详情

Extended Information