反应详情

A mixture of ethyl 5-bromo-1-n-butyl-1H-imidazole-4-carboxylate (0.10 g, 0.37 mmol), 2-methoxymethoxy-4-methoxyphenylboronic acid (0.16 g, 0.73 mmol), sodium carbonate (0.08 g, 0.73 mmol) and tetrakis(triphenylphosphine)palladium(0) (0.04 g) in 12 mL of toluene/ethanol/water (10/1/1) was stirred at reflux for 24 h. After an aqueous work up, extracting with ethyl acetate (3×20 mL), the combined organic extracts were washed with brine and dried (Na2SO4). After removing the solvent under reduced pressure, flash column chromatography (1:1 ethyl acetate/hexane) of the residue afforded the title compound as an oil (0.06 g, 46%). 1H NMR (250 MHz, CDCl3)δ 7.53 (s, 1H), 7.09 (d, 1H), 6.75 (d, 1H), 6.60 (dd, 1H), 5.05 (q, 2H), 4.21 (q, 2H), 3.85 (s, 3H) 3.80 (t, 2H), 3.30 (s, 3H) 1.60 (quintet, 2H), 1.30 (m, 5H), 0.80 (t, 3H).

1. temperatureat reflux for 24 h
2. extractionAfter an aqueous work up, extracting with ethyl acetate (3×20 mL)
3. washthe combined organic extracts were washed with brine
4. dry with materialdried (Na2SO4)
5. customAfter removing the solvent under reduced pressure, flash column chromatography (1:1 ethyl acetate/hexane) of the residue