Pyridine → 3-(Pyridin-3-yloxy)benzonitrile

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Cu(II) oxide (2.1 g, 26 mmol, 2.5 eq) was added to a mixture of 3-bromobenzonitrile (3.8 g, 21 mmol, 2.0 eq), 3-hydroxypyridine (1.0 g, 10 mmol, 1.0 eq), K2CO3 (3.0 g, 22 mmol, 2.1 eq) and pyridine (35 mL) at 80° C. The mixture was refluxed vigorously for 20 h and cooled to rt. CH2Cl2 was added and the mixture was filtered through celite. Pyridine was removed in vacuo and the residue dissolved in EtOAc and washed with 1N HCl (1×), 1N NaOH (1×), brine (1×), dried (MgSO4), filtered and concentrated in vacuo. Purification by flash chromatography on silica gel afforded 1.5 g (73%) of the title compound as a white solid: 1H NMR (400 MHz, DMSO-d6) δ 8.15 (dd, J=4.9, 1.6 Hz, 1H), 7.89 (td, J=7.6, 2.0 Hz, 1H), 7.69-7.67 (m, 2H), 7.61 (t, J=8.0 Hz, 1H), 7.51-7.49 (m, 1H), 7.17 (dd, J=7.0, 5.1 Hz, 1H), 7.12 (d, J=8.3 Hz, 1H); ES-MS [M+1]+: 197.2.

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