[CH3:1][C:2]1[CH:9]=[C:8](B2OC(C)(C)C(C)(C)O2)[CH:7]=[CH:6][C:3]=1[C:4]#[N:5].Br[C:20]1[CH:21]=[N:22][CH:23]=[CH:24][C:25]=1[CH:26]=[O:27].C(=O)([O-])[O-].[Na+].[Na+]>CN(C=O)C.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>[CH:26]([C:25]1[CH:24]=[CH:23][N:22]=[CH:21][C:20]=1[C:8]1[CH:7]=[CH:6][C:3]([C:4]#[N:5])=[C:2]([CH3:1])[CH:9]=1)=[O:27]
A mixture of 1a (430 mg, 1.769 mmol), 3-bromo-4-pyridinecarboxaldehyde (299 mg, 1.608 mmol), sodium carbonate (2N in water, 1.608 mL, 3.22 mmol), bis(triphenylphosphine)palladium(II) chloride (28.2 mg, 0.040 mmol) in DMF (6.432 mL) was heated to 100° C. for 2 hrs. The mixture was quenched with saturated NaHCO3 and extracted with EtOAc two times, dried over magnesium sulfate, filtered and concentrated. The residue was purified via Biotage (0-50% EtOAc/heptane; 25M column) giving compound 1b as white solid (280 mg, 78%). LC-MS (M+1) 223.1, t=1.28 min.
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