Carbazole → 2-(3-Carbazol-9-ylphenyl)-5-(3-methoxyphenyl)-1,3,4-oxadiazole

Participants

Reaction Steps

To a solution of 2-(3-iodophenyl)-5-(3-methoxyphenyl)-1,3,4-oxadiazole (3.0 g, 7.93 mmol), carbazole (1.5 g, 8.97 mmol), Cu (2.0 g, 31.47 mmol) in DMF (20.0 ml) was added potassium carbonate (4.0 g, 28.94 mmol) under nitrogen and stirring. Heating was started. The reaction was carried out at 150° C. for 5 h. After cooling, the reaction mixture was filtrated. The solid residues were carefully washed with THF. THF was evaporated from the combined filtration solution. Water (150.0 ml) was added, the brown solid product was obtained by filtration. The crude product was purified by silica gel column chromatography using dichloromethane/ethyl acetate (9.5:0.5) as eluent. After evaporating solvent, the white solid was recrystallized from acetone/methanol and finally dried under vacuum. Pure product was obtained as white solid in 3.15 g (95.4%) yield. 1H NMR (400 MHz, CDCl3, δ): 8.34 (m, 1H), 8.27 (m, 1 Hz), 8.18 (m, 2H), 7.78 (m, 2H), 7.71-7.65 (m, 2H), 7.46-7.41 (m, 5H), 7.36-7.31 (m, 2H), 7.09 (m, 1H), 3.89 (s, 3H, OCH3). 13C NMR (100 MHz, CDCl3, δ): 164.85, 163.84, 159.96, 140.60, 138.70, 130.85, 130.32, 130.25, 126.19, 125.84, 125.40, 124.72, 123.55, 120.45, 120.37, 119.39, 118.44, 111.52, 109.55, 55.55. [M]+ calcd for C39H26N4O2, 417.2. found 417.1.

Provenance & Evidence