Short-RInChIKey=SA-FUHFF-UHFFFADPSC-SFQRVUXRVN-UHFFFADPSC-NUHFF-NUHFF-NUHFF-ZZZ

2-Bromo-3-methylquinoxaline (60.0 mg, 269 μmol, 1.00 equiv), 2-ethynyl-3-methylquinoxaline (49.8 mg, 296 μmol, 1.10 equiv), dichloropalladium;triphenylphosphane (1.89 mg, 2.69 μmol, 0.0100 equiv) and copper(I) iodide (1.02 mg, 5.38 μmol, 0.0200 equiv) were loaded into a vial and dried for 10 minutes. Dry THF (1.2 mL) and triethylamine (81.7 mg, 112 μL, 807 μmol, 3.00 equiv) were added under argon atmosphere, and the resulting solution was degassed. The reaction was stirred at 25 °C for 3.8 days. The crude mixture was filtered on celite, then 10 mL of 1 M HCl was added. The aqueous phase was extracted with ethyl acetate (3 x 20 mL) and the collected organic layers were dried on Na2SO4. The solvent was removed under reduced pressure.