192945-49-6

基本信息
1H-吲唑-4-羧酸甲酯
1氫-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
物理化學(xué)性質(zhì)
安全數(shù)據(jù)
制備方法

18583-89-6

192945-49-6
以3-氨基-2-甲基苯甲酸甲酯為原料合成吲唑-4-甲酸甲酯的一般步驟如下:將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,隨后緩慢加入稀釋的冰醋酸水溶液(7mL,3mmol,冰醋酸與水的體積比為0.2:10)。反應(yīng)混合物在室溫下攪拌4-6小時(shí)。反應(yīng)完成后,用乙酸乙酯(EtOAc)萃取反應(yīng)混合物,并用去離子水(2×10mL)洗滌有機(jī)層。有機(jī)層經(jīng)無(wú)水硫酸鈉(Na2SO4)干燥后,減壓濃縮,并通過(guò)柱色譜法純化,得到黃色粉末狀產(chǎn)物吲唑-4-甲酸甲酯。產(chǎn)量為0.22g,產(chǎn)率69%;熔點(diǎn)為153-155℃。產(chǎn)物的1H NMR(400MHz,CDCl3,TMS為內(nèi)標(biāo),δ單位:ppm)數(shù)據(jù)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)。
參考文獻(xiàn):
[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