676448-17-2

基本信息
4-溴吲哚-1-羧酸叔丁酯
4-溴吲哚-1-羧基 酸 叔-丁基 酯
1-Boc-4-bromoindole
4-BROMOINDOLE, N-BOC PROTECTED
4-Bromo-1H-indole, N-BOC protected 95%
tert-butyl 4-bromo-1H-indole-1-carboxylate
4-BROMOINDOLE-1-CARBOXYLIC ACID TERT-BUTYL ESTER
4-BROMOINDOLE-1-CARBOXYLIC ACID TERT-BUTYL ESTER, 95+%
1H-Indole-1-carboxylic acid, 4-bromo-, 1,1-dimethylethyl ester
tert-Butyl 4-bromo-1H-indole-1-carboxylate, 4-Bromo-1-(tert-butoxycarbonyl)-1H-indole
物理化學(xué)性質(zhì)
制備方法

52488-36-5

24424-99-5

676448-17-2
以4-溴吲哚和二碳酸二叔丁酯為原料合成1-Boc-4-溴吲哚的一般步驟如下:將二碳酸二叔丁酯(17g,76.5mmol)緩慢加入到含有4-溴吲哚(10g,51mmol)和4-二甲氨基吡啶(DMAP,0.62g,0.51mmol)的四氫呋喃(THF,120mL)溶液中。反應(yīng)混合物在室溫下攪拌15分鐘后,通過旋轉(zhuǎn)蒸發(fā)去除溶劑。將殘余的油狀物溶于乙醚,并用去離子水進(jìn)行分配萃取。分離出的乙醚層依次用飽和碳酸氫鈉溶液(3×50mL)和鹽水(1×75mL)洗滌。洗滌后的乙醚層用無水硫酸鎂干燥,過濾后再次通過旋轉(zhuǎn)蒸發(fā)去除溶劑。所得的棕色油狀物通過硅膠柱色譜純化,洗脫劑為乙酸乙酯:己烷(1:100,v/v),最終得到15g(收率100%)的4-溴-吲哚-1-羧酸叔丁酯(1-Boc-4-溴吲哚)。
參考文獻(xiàn):
[1] Patent: US2004/72844, 2004, A1. Location in patent: Page/Page column 13-14
[2] Patent: CN107973780, 2018, A. Location in patent: Paragraph 0233; 0234; 0235; 0236
[3] Tetrahedron, 2009, vol. 65, # 34, p. 6877 - 6881
[4] Journal of Medicinal Chemistry, 2015, vol. 58, # 23, p. 9179 - 9195
[5] Tetrahedron Letters, 2017, vol. 58, # 15, p. 1499 - 1500