Pyrrole → HCID 21465587, compound

Participants

Reaction Steps

To an eggplant type flask (25 ml), 3-bromothiochromone (121 mg) prepared in Example 8, pyrrole (134 mg), potassium carbonate (1382 mg), and dimethylformamide (15 ml) were added. The mixture was reacted at 80° C. for 20 hours with stirring. The reaction mixture was added to ice water and extracted with chloroform. The organic layer was dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purifiedby the silica gel column chromatography and the purified product was recrystallized from benzene/hexane to give the titled compound (57.5 mg; yield=54.0%) as ocher crystals. Melting point: 135°-136 ° C. 1H-NMR(CDCl3, δ ppm): 7.02 (s, H3), 8.51 (dd, H5), 7.56 (t, H6), 7.61-7.68 (m, H7), 7.61-7.68 (m, H8), 7.22 (hr. t, H2'), 6.44 (br. t, H3'), 6.44 (br. t, H4'), 7.22 (br. t, H5').

Provenance & Evidence