192945-49-6

基本信息
1H-吲唑-4-羧酸甲酯
1氢-吲唑-4-甲酸甲酯
1H-吲唑-4-甲酸甲酯
Methyl indazole-4-carboxylate
4-(Methoxycarbonyl)-1H-indazole
METHYL 1H-INDAZOLE-4-CARBOXYLATE
INDAZOLE-4-CARBOXYLIC ACID METHYL ESTER
1H-Indazole-4-carboxylic acid, Methyl ester
4-(1H)INDAZOLE CARBOXYLIC ACID METHYL ESTER
物理化学性质
制备方法

18583-89-6

192945-49-6
以3-氨基-2-甲基苯甲酸甲酯为原料合成吲唑-4-甲酸甲酯的一般步骤如下:将3-氨基-2-甲基苯甲酸甲酯(0.3g,1.96mmol)溶于NaNO2水溶液(0.62g,2mmol)中,随后缓慢加入稀释的冰醋酸水溶液(7mL,3mmol,冰醋酸与水的体积比为0.2:10)。反应混合物在室温下搅拌4-6小时。反应完成后,用乙酸乙酯(EtOAc)萃取反应混合物,并用去离子水(2×10mL)洗涤有机层。有机层经无水硫酸钠(Na2SO4)干燥后,减压浓缩,并通过柱色谱法纯化,得到黄色粉末状产物吲唑-4-甲酸甲酯。产量为0.22g,产率69%;熔点为153-155℃。产物的1H NMR(400MHz,CDCl3,TMS为内标,δ单位:ppm)数据如下:δ2.55(s,3H),7.37(t,1H,J=14.32Hz),7.53(s,1H),7.67(d,1H,J=8.12Hz),7.82(d,1H,J=8.16Hz),9.79(s,1H)。
参考文献:
[1] Patent: US2012/130078, 2012, A1. Location in patent: Page/Page column 4-5
[2] Patent: EP2141150, 2010, A1. Location in patent: Page/Page column 48
[3] Journal of Medicinal Chemistry, 2000, vol. 43, # 1, p. 41 - 58
[4] Asian Journal of Chemistry, 2014, vol. 26, # 7, p. 1921 - 1930
[5] Patent: WO2009/108838, 2009, A1. Location in patent: Page/Page column 104