Triethylamine → 6-chloro-3-methyl-2-(2-methyl-5-pyrrolidin-1-yl-2H-[1,2,4]triazol-3-ylethynyl)-quinoxaline

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To a stirred solution of 2-bromo-6-chloro-3-methylquinoxaline with 3-bromo-6-chloro-2-methylquinoxaline (250 mg, 485 μmol, Eq: 1.00) and 5-Ethynyl-1-methyl-3-pyrrolidin-1-yl-1H-[1,2,4]triazole (94.1 mg, 534 μmol, Eq: 1.1) at room temperature in N,N-dimethylformamide (7.5 ml) under an argon atmosphere were added triethylamine (98.2 mg, 135 μl, 971 μmol, Eq: 2), copper (I) iodide (4.62 mg, 24.3 μmol, Eq: 0.05) and bis(triphenylphosphine)palladium (II) chloride (17.0 mg, 24.3 μmol, Eq: 0.05). The mixture was purged with argon before it was stirred over weekend at room temperature (dark sol.). The mixture was stirred over an additional night at 80° C. The crude material was applied on silica gel and purified by column chromatography. After separation of the isomers by preparative HPLC gave 6-chloro-3-methyl-2-(2-methyl-5-pyrrolidin-1-yl-2H-[1,2,4]triazol-3-ylethynyl)-quinoxaline (9.3 mg, 5.4%) as a yellow solid. MS: m/z=353.5 (M+H+)

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