Br[C:2]1[CH:3]=[CH:4][C:5]([C:8]#[N:9])=[N:6][CH:7]=1.[C:10]1(B(O)O)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.C(=O)([O-])[O-].[Na+].[Na+].C1C=CC=CC=1>C(P[Pd](PC(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)(PC(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)PC(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C(O)C>[C:10]1([C:2]2[CH:3]=[CH:4][C:5]([C:8]#[N:9])=[N:6][CH:7]=2)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1A mixture comprising 5-bromopyridine-2-carbonitrile (0.09 g, 0.49 mmol), phenyl boronic acid (0.12 g, 0.98 mmol), 2M sodium carbonate ((0.98 mL, 1.96 mmol), tetrakis(tritylphosphanyl)palladium (0.06 g, 0.049 mmol), benzene (2 mL) and ethanol (2 mL) was heated at reflux for 1 hour and then partitioned between ethyl acetate and water. The organic layer was separated, washed with water, dried (MgSO4) and concentrated. The residue was purified by silica gel chromatography (25% ethyl acetate/hexanes) to provide 5-phenylpyridine-2-carbonitrile (0.12 g, 0.67 mmol). MS (CI), Calculated for C12H8N2, 180.2, Found (MH+): 182.
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