Br[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([C:12]([N:14]([O:16][CH3:17])[CH3:15])=[O:13])[CH:10]=2)[N:5]=[CH:4][CH:3]=1.[CH:18](/B(O)O)=[CH:19]\[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.COC1C=CC=C(OC)C=1C1C=CC=CC=1P(C1CCCCC1)C1CCCCC1.[O-]P([O-])([O-])=O.[K+].[K+].[K+].O>C1COCC1.C(Cl)Cl.O.CC([O-])=O.CC([O-])=O.[Pd+2]>[CH3:17][O:16][N:14]([CH3:15])[C:12]([C:9]1[CH:10]=[C:11]2[C:6](=[CH:7][CH:8]=1)[N:5]=[CH:4][CH:3]=[C:2]2/[CH:18]=[CH:19]/[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[O:13]A mixture of 4-bromo-N-methoxy-N-methylquinoline-6-carboxamide (155 mg, 0.525 mmol), (E)-styrylboronic acid (155 mg, 1.05 mmol), Pd(OAc)2 (11.8 mg, 0.053 mmol), SPhos (43 mg, 0.105 mmol) and K3PO4.H2O (334 mg, 1.58 mmol) in anhydrous THF (5 mL) was heated at 35° C. overnight. The reaction was diluted with DCM and water. The organics were washed with water and concentrated. The resulting residue was purified by silica column chromatography (40-55% EtOAc/hexanes) to yield (E)-N-methoxy-N-methyl-4-styrylquinoline-6-carboxamide. (ES, m/z) 319.0 [M+H]+
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