Potassium Carbonate → 1-{3-[6-Chloro-2-(4-fluorophenyl)-1H-indol-1-yl]-1-oxopropyl}-4-(2-methoxyphenyl)piperazine

Participants

Reaction Conditions

Reaction Steps

A mixture of 6-chloro-2-(4-fluorophenyl)-1H-indole (Description 26, 348 mg, 1.4 mmol), 4-(2-methoxyphenyl)-1-(1-oxo-2-propenyl)piperazine (Description 25, 400 mg, 1.6 mmol) and potassium carbonate (1.5 g, 10.8 mmol) in dimethylformamide was stirred at 100° C. for 48 h. The mixture was cooled and aqueous ammonium chloride (saturated, 10 mL) and water (30 mL) were added. The mixture was extracted with ethyl acetate and the combined organic fractions were dried (MgSO4) and the solvent was evaporated under reduced pressure. The residue was purified by flash column chromatography on silica gel, eluting with isohexane/EtOAc (50:50), to give the title compound. 1H NMR (360 MHz, CDCl3) δ 7.51 (1H, d, J 8.4 Hz), 7.45 (3H, m), 7.18 (2H, t, J 8.7 Hz), 7.11 (1H, dd, J 8.4, 1.8 Hz), 7.01 (1H, m), 6.93-6.81 (3H, m), 6.48 (1H, s), 4.51 (2H, t, J 7.7 Hz), 3.85 (3H, s), 3.72 (2H, t, J 5.0 Hz), 3.30 (2H, t, J 5.0 Hz), 2.93 (2H, t, J 5.0 Hz), 2.79 (2H, t, J 5.0 Hz), and 2.56 (2H, t, J 7.7 Hz). m/z (ES+) 492, 494 (M+1).

Provenance & Evidence