Br[C:2]1[CH:3]=[C:4]([N+:10]([O-:12])=[O:11])[C:5]([O:8][CH3:9])=[N:6][CH:7]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[CH2:19]([N:22]([CH3:24])[CH3:23])[C:20]#[CH:21]>CN(C=O)C.CC#N.CC#N.Cl[Pd]Cl>[CH3:9][O:8][C:5]1[N:6]=[CH:7][C:2]([C:21]#[C:20][CH2:19][N:22]([CH3:24])[CH3:23])=[CH:3][C:4]=1[N+:10]([O-:12])=[O:11]To a solution of 5-bromo-2-methoxy-3-nitropyridine (1.50 g, 6.44 mmol) in DMF (30 mL) were added bis(acetonitrile)palladium(II)chloride (83.5 mg, 0.322 mmol), 2-dicyclohexylphosphino-2′,4′,6′-tri-i-propyl-1-1′-biphenyl (399 mg, 0.837 mmol), cesium carbonate (4.19 g, 12.9 mmol) and propargyl(dimethylamine) (0.832 mL, 7.72 mmol). The reaction mixture was flushed with nitrogen gas and allowed to stir for 4 h at 50° C. The reaction mixture was diluted with EtOAc and washed with brine, dried over Na2SO4, filtered and concentrated. The residue was purified by column chromatography to give 3-(6-methoxy-5-nitropyridin-3-yl)-N,N-dimethylprop-2-yn-1-amine (0.41 g, 27%) as a white solid. LCMS (FA): Rt=0.85 min, m/z=236.2 (M+H).
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