[NH2:1][C:2]1[N:9]=[CH:8][C:7](Br)=[CH:6][C:3]=1[CH:4]=[O:5].[C:11]([C:13]1[CH:14]=[C:15](B(O)O)[CH:16]=[CH:17][CH:18]=1)#[N:12].C([O-])([O-])=O.[K+].[K+].O>CC#N.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[NH2:1][C:2]1[N:9]=[CH:8][C:7]([C:17]2[CH:18]=[C:13]([CH:14]=[CH:15][CH:16]=2)[C:11]#[N:12])=[CH:6][C:3]=1[CH:4]=[O:5]2-amino-5-bromonicotinaldehyde (0.1 g, 0.5 mmol), 3-cyanophenylboronic acid (0.146 g, 1.0 mmol), dichlorobis(triphenylphosphine)palladium(II) (0.017 g, 0.02 mmol), and K2CO3 (0.14 g, 1.0 mmol) were combined in 3 mL of 4:1 CH3CN:H2O and heated to 150° C. for 5 minutes in the SmithSynthesizer™ microwave instrument. Upon cooling, the reaction mixture was chromatographed on silica gel eluting with hexanes/ethyl acetate (0% EtOAc to 100% EtOAc over 10 minutes) to afford 3-(6-amino-5-formylpyridin-3-yl)benzonitrile (46 mg) as a solid.
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