Br[C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=O.Cl.[CH3:11][O:12][C:13]1[CH:18]=[CH:17][C:16]([NH:19][NH2:20])=[CH:15][CH:14]=1.CC(C)([O-])C.[Na+]>C1(C)C=CC=CC=1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2]>[CH3:11][O:12][C:13]1[CH:18]=[CH:17][C:16]([N:19]2[C:2]3[C:3](=[CH:6][CH:7]=[CH:8][CH:9]=3)[CH:4]=[N:20]2)=[CH:15][CH:14]=12-Bromobenzaldehyde (74 mg, 0.4 mmol), 4-methoxyphenylhydrazine hydrochloride (70 mg, 0.4 mmol), sodium tert-butoxide (115 mg, 1.2 mmol), palladium(II) acetate (18 mg, 0.08 mmol) and 1,1′-bis(diphenylphosphino)ferrocene (44 mg, 0.08 mmol) were dissolved in toluene (0.6 mL) and heated to 100° C. overnight. The mixture was filtered through Celite with ethyl acetate, and the filtrate was concentrated. SiO2 chromatography (5-20% ethyl acetate/hexanes) gave the desired product, 30 mg. LC-MS (C14H12N2O calculated 224) m/z 225 (M+H).
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