反应 #47781

反应方程式

lithium hydroxide

5-Bromo-3-(4-ethoxy-3-methyl-phenoxymethyl)-4′-methoxy-biphenyl

4-trifluoromethoxyphenylboronic acid

Potassium carbonate

→

[4-(4-methoxy-4″-trifluoromethoxy-[1,1′;3′,1″]terphenyl-5′-ylmethoxy)-2-methyl-phenoxy]-acetic acid

溶剂

dioxane

ethanol

water

反应条件

后处理

1. 1
   其他(170° C. for 10 min)
2. 2
   温度Cooling
3. 3
   workup.STIRRINGstirring for 3 hours at room temperature
4. 4
   其他followed by reversed-phase purification

实验过程

5-Bromo-3-(4-ethoxy-3-methyl-phenoxymethyl)-4′-methoxy-biphenyl 15 (50 mg, 0.11 mmol) and 4-trifluoromethoxyphenylboronic acid (30 mg, 0.15 mmol, 1.3 equiv.) are dissolved in dioxane (0.5 mL). Potassium carbonate (38 mg, 0.27 mmol), water (0.05 mL) and ethanol (0.05 mL) are added, followed by tetrakis (triphenylphosphino)palladium (15.6 mg, 0.13 mmol). The mixture is stirred under nitrogen and subjected to microwave (170° C. for 10 min). Cooling, addition of 0.25 mL of aqueous 1N lithium hydroxide solution, and stirring for 3 hours at room temperature, followed by reversed-phase purification yielded [4-(4-methoxy-4″-trifluoromethoxy-[1,1′;3′,1″]terphenyl-5′-ylmethoxy)-2-methyl-phenoxy]-acetic acid A2. 1H-NMR (400 MHz, CDCl3) δ=7.50 (m, 3H), 7.42 (m, 4H), 7.17 (d, J=8.0 Hz, 2H), 6.87 (d, J=8.0 Hz, 2H), 6.75 (d, J=2.8 Hz, 1H), 6.65 (dd, J=8.8, 2.8 Hz, 1H), 6.58 (d, J=8.8 Hz, 1H), 5.17 (s, 2H), 4.50 (s, 2H), 3.73 (s, 3H), 2.16 (s, 3H). 19F-NMR (376 MHz, CDCl3) δ=−57.8. MS calculated for C30H26F3O6 (M+H+) 539.17. found 539.0.

来源