10601-19-1 5-甲氧基吲哚-3-甲醛

危险性质：非危险化学品

化学合成。

医药

合成路线 1（1. 合成：10601-19-1）

产率：94% 合成条件：Stage #1: at 0℃; for 1 h; Stage #2: at 20℃; for 5 h; Stage #3: With sodium hydroxide In N,N-dimethyl-formamide at 100℃; for 0.17 h; 实验步骤：一般程序：在搅拌下以逐滴方式将草酰氯（0.3mL）加入冷却的（冰浴）DMF（3mL）中。 然后将混合物在0℃下搅拌1小时。 然后将取代的吲哚（4mmol）的DMF（1.5mL）溶液以逐滴的方式加入到反应混合物中。 将得到的混合物在室温下搅拌5小时。 然后加入2N氢氧化钠溶液（2mL），并将混合物在100℃加热10分钟。 然后将混合物冷却并用乙酸乙酯（3×50mL）萃取。 合并有机层，依次用水和盐水洗涤。 将有机物干燥（Na 2 SO 4）并蒸馏至干，得到粗残余物，将其通过快速柱色谱法纯化，使用乙酸乙酯/石油醚（3：1，v / v）作为洗脱剂，得到纯的吲哚-3-甲醛。（图4a-K）。 参考文献：

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合成路线 2（2. 合成：10601-19-1）

产率：60% 合成条件：With silica supported ceric ammonium nitrate In acetonitrile for 15 h; Reflux 实验步骤：通用方法：将吲哚（1mmol），HMTA（2.5mmol）和10％CAN-SiO 2的混合物在CH 3 CN（5.0mL）中回流。 反应完成后，蒸发混合物，得到粗制的CAN-SiO2残余物和产物。 将粗残余物用EtOAc（10mL，5）洗涤并干燥，得到粗产物，将其通过快速柱色谱法（EtOAc /己烷= 1：3）纯化。 参考文献：

• [1] Tetrahedron Letters, 2017, vol. 58, # 30, p. 2877 - 2880 [2] Tetrahedron Letters, 2014, vol. 55, # 29, p. 3909 - 3912 [3] Bioorganic and Medicinal Chemistry Letters, 2012, vol. 22, # 18, p. 5909 - 5914

合成路线 3（3. 合成：10601-19-1）

产率：72% 合成条件：With water; iodine; oxygen; sodium carbonate In 1,4-dioxane at 100℃; for 36 h; Schlenk technique; Sealed tube 实验步骤：一般程序：在空气中，向装有搅拌棒的20mL Schlenk管中加入吲哚1（0.2mmol，1当量），TMEDA（75μL，0.5mmol，2.5当量），Na 2 CO 3（42.4mg，0.4mmol， 2.0当量），1,4-二恶烷（0.5mL）和H 2 O（100μL）。 然后加入I 2（101.5mg，0.4mmol，2.0当量），用橡胶塞密封管并加入O 2。 将反应混合物在100℃下在油浴中搅拌36小时。 冷却至室温后，将得到的混合物在减压下用EtOAc（20mL）蒸发，并将残余物通过硅胶快速柱色谱法纯化，得到产物。 参考文献：

• [1] Tetrahedron Letters, 2014, vol. 55, # 41, p. 5618 - 5621