General procedure for the synthesis of 3-methoxy-4-(4-methyl-1H-imidazol-1-yl)benzaldehyde from 4-methylimidazole and 3-methoxy-4-fluorobenzaldehyde: 4-fluoro-3-methoxybenzaldehyde (85 g, 0.55 mol), 4-methyl-1H-imidazole (90.5 g, 1.1 mol) and cesium carbonate (268.8 g, 0.82 mol) were mixed in dimethylformamide (1.7 L) were mixed and the reaction was stirred at 100 °C for 1 hour. After completion of the reaction, the mixture was cooled to room temperature, filtered, and the filtrate was concentrated under reduced pressure. The concentrated residue was dissolved in water (2 L) and extracted with ethyl acetate (3 x 2 L). The organic layers were combined, washed sequentially with water and brine, dried over anhydrous sodium sulfate and concentrated under reduced pressure to remove the solvent. Purification by silica gel column chromatography (eluent ratio petroleum ether:ethyl acetate = 2:1) gave a yellow solid. The solid was recrystallized with ethyl acetate (300 mL) to give 3-methoxy-4-(4-methyl-1H-imidazol-1-yl)benzaldehyde in white solid form. Yield: 17.8 g, 0.082 mol, 15% yield.1H NMR (300 MHz, CDCl3) δ 2.31 (d, J = 1.0 Hz, 3H), 3.97 (s, 3H), 7.01 (m, 1H), 7.45 (d, J = 7.8 Hz, 1H), 7.54-7.58 (m, 2H), 7.83 (d, J = 1.3 Hz, 1H), 10.01 (s, 1H).
