Cesium carbonate → (5-Bromopyrazin-2-yl)-(6-trifluoromethyl-pyridin-3-yl)-amine

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Reaction Conditions

Reaction Steps

Pd(OAc)2 (0.097 g, 0.432 mmol) and Xantphos (0.25 g, 0.432 mmol) were added to a solution of 2,5-dibromopyrazine (2.05 g, 8.64 mmol) in 15 mL of toluene under argon atmosphere, followed by cesium carbonate (8.44 g, 25.9 mmol) and 6-(trifluoromethyl)pyridin-3-amine (1.4 g, 8.64 mmol). The mixture was degassed for 10 min. The reaction mixture was stirred at 100° C. for 4 h, allowed to warm to room temperature, and diluted with ethyl acetate and water. The separated organic layer was dried over sodium sulfate and filtered, and the filtrate was concentrated under reduced pressure. The crude product was purified by flash chromatography using 20% ethyl acetate in hexane to afford the title compound (1 g, 36%) as a white solid. 1H NMR (300 MHz, DMSO-d6) δ 10.34 (s, 1H), 8.88 (d, J=2.5 Hz, 1H), 8.47-8.35 (m, 2H), 8.17 (d, J=1.4 Hz, 1H), 7.84 (d, J=8.7 Hz, 1H). ESI-MS m/z: 319 (M+H)+.

Provenance & Evidence