反应详情

Ethyl 5-bromo-4-methyl-1-[(4-methylphenyl)sulfonyl]-1H-pyrrole-3-carboxylate (1.0 g), phenylboronic acid (473 mg), sodium carbonate (823 mg) and tetrakis(triphenylphosphine)palladium (299 mg) were suspended in a mixture of 1,2-dimethoxyethane (10 mL) and distilled water (10 mL), and the mixture was refluxed under a nitrogen atmosphere for 16 hr. The reaction mixture was filtrated, water was added to the filtrate and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: hexane-ethyl acetate=9:1→1:1) to give the title compound as a pale-brown oil (yield 430 mg, 42%).

1. distillationdistilled water (10 mL)
2. temperaturethe mixture was refluxed under a nitrogen atmosphere for 16 hr
3. filtrationThe reaction mixture was filtrated
4. additionwater was added to the filtrate
5. extractionthe mixture was extracted with ethyl acetate
6. washThe extract was washed with saturated brine
7. dry with materialdried over anhydrous sodium sulfate
8. concentrationconcentrated under reduced pressure
9. customThe residue was purified by silica gel column chromatography (eluent: hexane-ethyl acetate=9:1→1:1)