反应 #7088

反应方程式

3-chlorophenylboronic acid

sodium carbonate

5-bromo-3-methoxy-3-prop-1-ynyl-1,3-dihydroindol-2-one

→

title compound

收率 15.0%

5-(3-Chloro-phenyl)-3-methoxy-3-prop-1-ynyl-1,3-dihydro-indol-2-one

收率 15.0%

溶剂

water

dimethoxyethane

water

反应条件

后处理

1. 1
   温度the mixture heated
2. 2
   温度under reflux
3. 3
   workup.WAITAfter 16 h
4. 4
   温度the mixture was cooled
5. 5
   萃取extracted with EtOAc (×3)
6. 6
   洗涤The combined organic layers were washed with sodium hydroxide (1N, ×2), brine
7. 7
   干燥dried (MgSO4)
8. 8
   其他evaporated
9. 9
   洗涤The residue was subjected to column chromatography (SiO2, EtOAc: hexane, gradient elution)
10. 10
    其他the product triturated with hexane

实验过程

5-bromo-3-methoxy-3-prop-1-ynyl-1,3-dihydroindol-2-one (0.56 g, 2.0 mmol) and tetrakis(triphenylphosphine)palladium(0) (0.12 g, 0.10 mmol) were stirred at room temperature in dimethoxyethane (22 cm3). After 15 min. 3-chlorophenylboronic acid (0.63 g, 4.0 mmol) and sodium carbonate (1.06 g, 10 mmol) in water (11 cm3) were added and the mixture heated under reflux. After 16 h, the mixture was cooled, poured into water and extracted with EtOAc (×3). The combined organic layers were washed with sodium hydroxide (1N, ×2), brine, dried (MgSO4) and evaporated. The residue was subjected to column chromatography (SiO2, EtOAc: hexane, gradient elution) and the product triturated with hexane to afford the title compound (0.095 g, 0.30 mmol, 15%) as a solid: mp.>190° C. (decomp.); (CDCl3) δ 1.88 (s, 3H), 3.25 (s, 3H), 3.30 (s, 1H), 6.91 (d, 1H, J=8.1 Hz), 7.29–7.39 (m, 2H), 7.44–7.47 (m, 1H), 7.54–7.57 (m, 2H), 7.74 (d, 1H, J=1.7 Hz); MS (EI) m/z 311 (M+).

来源