Sodium Carbonate → 3-Methyl-5-pyridin-3-yl-3H-benzooxazol-2-one

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A mixture of pyridin-3-ylboronic acid (61.5 mg, 0.5 mmol), 5-Bromo-3-methyl-3H-benzooxazol-2-one (114 mg, 0.5 mmol), polymer-supported Pd(PPh3)4 (0.11 mmol/g, 114 mg, 0.0125 mmol), Na2CO3 (2 M in water, 0.5 mL, 1 mmol) in DME (3 mL) was heated to reflux for 6 hrs. After filtration and concentration, the residue was purified by flash column (MeOH—CH2Cl2, v/v, 1-3%) and yielded the title compound as pale yellow solid (45 mg). 1HNMR(CDCl3, 400.342 MHz): δ 3.47 (s, 3H), 7.13 (s, 1H), 7.30 (m, 2H), 7.38 (dd, J=4.8, 7.9 Hz, 1H), 7.85 (m, 1H), 8.62 (dd, J=1.5, 4.8 Hz, 1H), 8.82 (d, J=2.4 Hz, 1H).

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