Water → 2-(3-Methoxy-4-pyridin-3-ylphenyl)-1,3-benzoxazole

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The solution of 4-(1,3-benzoxazol-2-yl)-2-methoxyphenyl trifluoromethanesulfonate (148 mg, 0.4 mmol) in 6 mL of 2:1 DMF:H2O was degassed via Argon for 10 min. Then K2CO3 (137 mg, 0.99 mmol), Pd(Ph3P)4 (23 mg, 0.02 mmol), n-Bu4NBr (128 mg, 0.40 mmol) and 3-Pyridylboronic acid (73 mg, 0.60 mmol) were added at 22° C. The resulting mixture was then heated at 75° C. for 1 h under Argon. Cooled the reaction mixture to 22° C., then filtered through a pad of Celite. The filtrate was concentrated under reduced pressure to give after purification by flash chromatography (silica gel, 3:1; hexanes:EtOAc) the desired compound as a yellow solid. 1H NMR (CDCl3, 300 MHz) δ 8.83 (d, 1H), 8.60 (dd, 1H), 7.92 (m, 3H), 7.81 (m, 1H), 7.62 (m, 1H), 7.48 (d, 1H), 7.39 (m, 3H), 3.98 (s, 3H). MS (ESI) 303 (M+H)+.

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