反应 #2024124

反应方程式

5-bromo-spiro[cyclopentane-1,3′-[3H]indol]-2′(1′H)-one

3-nitrophenylboronic acid

sodium carbonate

→

title compound

收率 123.6%

5′-(3-nitrophenyl)spiro[cyclopentane-1,3′-[3H]indol]2′(1′H)-one Spiro[cyclopentane-1,3′-[3H]indol]-2′(1′H)-one

收率 123.6%

溶剂

dimethoxyethane

water

water

反应条件

后处理

1. 1
   温度to reflux for 3 h
2. 2
   萃取extracted with EtOAc (×3)
3. 3
   洗涤The combined organic extracts were washed with water, brine
4. 4
   干燥dried (MgSO4)
5. 5
   其他evaporated
6. 6
   其他The residue was purified by column chromatography (SiO2, ethyl acetate: hexane 1:3)

实验过程

A solution of 5-bromo-spiro[cyclopentane-1,3′-[3H]indol]-2′(1′H)-one (0.3 g, 1.1 mmol) and tetrakis(triphenylphosphine)palladium(0) (0.07 g, 0.06 mmol) in dimethoxyethane (8 cm3) was stirred under N2 for 20 min. To this mixture was then added 3-nitrophenylboronic acid (0.23 g, 1.4 mmol) and sodium carbonate (0.36 g, 3.4 mmol) in water (3 cm3). The solution was brought to reflux for 3 h then cooled to RT, poured into water and extracted with EtOAc (×3). The combined organic extracts were washed with water, brine, dried (MgSO4), and evaporated. The residue was purified by column chromatography (SiO2, ethyl acetate: hexane 1:3) to afford the title compound (0.21 g, 0.68 mmol, 62%) as a yellow solid: mp. 238-240 C.; 1H NMR (DMSO-d6) δ1.89-1.99 (m, 8H), 6.96 (d, J=8.1 Hz, 1H), 7.58 (dd, J=8.1, 1.8 Hz, 1H), 7.66 (d, J=1.8 Hz, 1H), 7.71 (dd, J=8.0, 8.0 Hz, 1H), 8.13 (dd, J=7.0, 1.0 Hz, 2H), 8.4 (d, J=1.8 Hz, 1H), 10.42 ( br s, 1H); 13C NMR (dioxane-d8) δ26.31, 38.13 (t), 53.85 (s), 108.9, 121.15, 121,33, 126.23, 129.38, 132.11 (d), 132.6, 138.32, 141.84, 142.74, 149.14, 182.68 (s); MS (EI) m/z 308 (M)+.

来源