Реакция #2146790

Уравнение реакции

[6-methoxy-2-(1H-pyrazol-4-yl)-benzofuran-3-yl]-(3,4,5-trimethoxyphenyl)-methanone

dichloromethane

4-methoxy-phenyl boronic acid

oxygen

→

product

Выход 15.0%

{6-Methoxy-2-[1-(4-methoxy-phenyl)-1H-pyrazol-4-yl]-benzofuran-3-yl}-(3,4,5-trimethoxyphenyl)-methanone

Выход 15.0%

Растворители

pyridine

Условия реакции

Обработка

1. 1
   ДругоеTo an 8 mL screw cap glass vial
2. 2
   Другоеcap
3. 3
   ФильтрацияAfter this time the reaction mixture was filtered through celite
4. 4
   Концентрированиеthe filtrate was concentrated
5. 5
   Другоеpurified by silica-gel flash chromatography (eluent=hexane:ethyl acetate, 3:1)

Методика

To an 8 mL screw cap glass vial was added [6-methoxy-2-(1H-pyrazol-4-yl)-benzofuran-3-yl]-(3,4,5-trimethoxyphenyl)-methanone (11 mg, 0.027 mmol), 3 Å molecular sieves, dichloromethane (0.5 mL), cupric acetate (10 mg, 0.054 mmol), 4-methoxy-phenyl boronic acid (9 mg, 0.059 mmol) and pyridine (15 μl, excess) and the capped vial was shaken at room temperature for two days with occasional removal of the cap to expose the mixture to atmospheric oxygen. After this time the reaction mixture was filtered through celite and the filtrate was concentrated and purified by silica-gel flash chromatography (eluent=hexane:ethyl acetate, 3:1) to afford the product as a yellow solid (2 mg, 15% yield). 1H-NMR (CDCl3) δ 8.56 (s, 1H), 8.17 (s, 1H), 7.60 (d, J=8.9 Hz, 2H), 7.15 (s, 2 H), 7.14 (d, J=8.7 Hz, 1H), 7.07 (d, J=2.0 Hz, 1H), 6.96 (d, J=8.9 Hz, 2H), 6.81 (dd, J=8.7, 2.0 Hz, 1H), 3.92 (s, 3H), 3.87 (s, 3H), 3.84 (s, 3H), 3.78 (s, 6H).

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