Sodium Carbonate → 5-Bromo-2-methyl-3-phenylquinoxaline

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A suspension of 5-bromo-3-chloro-2-methylquinoxaline (126e; 327 mg, 1.270 mmol), phenylboronic acid (Aldrich; 155 mg, 1.270 mmol), Na2CO3 (673 mg, 6.35 mmol), and Pd(PPh3)4 (Strem Chemicals, Inc.; 73.4 mg, 0.063 mmol) in a mixture of CH3CN (9.00 mL) and water (3 mL) was stirred under argon at 80° C. for 16 h. The reaction was cooled to RT and concentrated onto silica gel. Chromatographic purification (silica gel, 0-40% EtOAc/hexanes) furnished 5-bromo-2-methyl-3-phenylquinoxaline (340.0 mg, 1.136 mmol, 89% yield) as a peach-colored solid. 1H NMR (400 MHz, CDCl3) δ ppm 8.03 (2H, d, J=7.8 Hz), 7.77 (2H, dd, J=7.9, 1.7 Hz), 7.60 (1H, d, J=7.8 Hz), 7.48-7.57 (3H, m), 2.85 (3H, s). m/z (ESI, +ve) 298.9/300.8 (M+H)+.

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