Sodium Carbonate → 2-[4-(6-Chloropyridin-3-yl)-3-methoxyphenyl]-1,3-benzoxazole

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Utilizing the general procedure outlined in the synthesis of 2-[4-(6-bromopyridin-2-yl)-3-methoxyphenyl]-1,3-benzoxazole, 2-[3-methoxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-1,3-benzoxazole (100 mg, 0.29 mmol) was reacted with 5-bromo-2-chloropyridine (55 mg, 0.29 mmol) and Na2CO3 (90 mg, 0.86 mmol) in DME (2 mL), and H2O (2 mL) to afford the desired 2-[4-(6-chloropyridin-3-yl)-3-methoxyphenyl]-1,3-benzoxazole as a colorless solid: 1H NMR (CDCl3, 300 MHz) δ 8.59 (d, 1H), 7.85–7.66 (m, 3H), 7.44–7.78 (m, 1H), 7.56–7.60 (m, 1H), 7.48–7.45 (d, 1H), 7.42–7.38 (m, 3H), 3.98 (s, 3H). MS (ESI) 337 (M+H)+.

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