Potassium Carbonate → HCID 178516131, compound

Participants

Reaction Steps

To a flask with 6-bromo-4-hydroxy-2-trifluoromethyl-quinoline (1.00 g, 3.42 mmol) was added K2CO3 (8.55 mL, 1.0 M in H2O, 8.55 mmol) followed by dioxane (85.5 mL). Benzofuran-2-boronic acid (0.665 g, 4.10 mmol) was then added followed by PdCl2(dppf) (0.028 g, 0.0342 mmol). The reaction mixture was stirred at room temperature for 0.5 hour and then heated to 65° C. for 18 hours. After concentration, the reaction was diluted with EtOAc (200 mL). The organic layer was washed with 1 N HCl, (20 mL), sat. aq. NaHCO3 (20 mL), and brine (20 mL) and then dried (MgSO4). After concentration, the residue was recrystallized from EtOAc to afford the product (0.770 g, 68%) as a solid. Mass spectrum (+ESI, [M+H]+) m/z 330. 1H NMR (500 MHz, DMSO-d6): δ 8.68 (s, 1H), 8.37 (d, 1H, J=9.3 Hz), 8.07 (d, 1H, J=9.3 Hz), 7.65-7.75 (m, 3H), 7.38 (t, 1H, J=7.7 Hz), 7.30 (t, 1H, J=7.7 Hz), and 7.06 ppm (s, 1H).

Provenance & Evidence