893441-86-6
893441-86-6 结构式
基本信息
N-BOC-吲哚-4-频哪醇硼酸酯
1-Boc-indole-4-boronic Acid Pinacol Ester
1-tert-Butoxycarbonyl-indole-4-boronic acid pinacol ester
tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)indole-1-carboxylate
tert-Butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole-1-carboxylate
1H-Indole-1-carboxylic acid, 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-, 1,1-dimethylethyl ester
物理化学性质
制备方法
676448-17-2
73183-34-3
893441-86-6
向4-溴-1H-吲哚-1-羧酸叔丁酯（9 g, 30 mmol）和双（频哪醇合）二硼（8.45 g, 33 mmol）的DMSO（180 mL）溶液中加入KOAc（9 g, 91 mmol）。在加入Pd(dppf)Cl2（744 mg, 912 μmol）之前，用氮气（3次）吹扫悬浮液。将反应混合物在80℃下搅拌12小时。反应完成后，将悬浮液倒入水（400 mL）中并用EtOAc（300 mL × 2）萃取。合并的有机层用盐水（200 mL）洗涤，经Na2SO4干燥并减压浓缩。粗产物通过硅胶柱层析（PE:EtOAc = 40:1）纯化，得到4-(4,4,5,5-四甲基-1,3,2-二氧杂硼杂环戊烷-2-基)-1H-吲哚-1-羧酸叔丁酯（7.8 g, 22.7 mmol, 75.8%收率），为白色固体。NMR（CDCl3, 400 MHz）δ ppm: 1.38（s, 12H）, 1.68（s, 9H）, 7.09（d, J = 3.6 Hz, 1H）, 7.30（t, J = 7.6 Hz, 1H）, 7.61（d, J = 3.2 Hz, 1H）, 7.70（d, J = 7.2 Hz, 1H）, 8.24（d, J = 8 Hz, 1H）; ESIMS实测值C19H26BNO4 [M+H]+ 344.1。
参考文献：
[1] Patent: WO2017/23993, 2017, A1. Location in patent: Paragraph 0687; 0688
[2] Patent: WO2017/23986, 2017, A1. Location in patent: Paragraph 0705; 0706
[3] Patent: WO2017/23973, 2017, A1. Location in patent: Paragraph 0704
[4] Patent: WO2017/24026, 2017, A1. Location in patent: Paragraph 0686; 0687