Cl.[Cl:2][C:3]1[N:10]=[CH:9][CH:8]=[CH:7][C:4]=1[CH2:5]Cl.N1C=CC=CC=1.[CH3:17][O:18][C:19]1[CH:24]=[CH:23][C:22]([NH2:25])=[CH:21][CH:20]=1.[OH-:26].[Na+]>C(Cl)(Cl)Cl.CCOC(C)=O>[Cl:2][C:3]1[C:4]([C:5]([NH:25][C:22]2[CH:23]=[CH:24][C:19]([O:18][CH3:17])=[CH:20][CH:21]=2)=[O:26])=[CH:7][CH:8]=[CH:9][N:10]=12-Chloronicotinyl chloride hydrochloride (2.94 g, 16.5 mmol) was added in portions to a solution of pyridine (4.0 mL) and 4-anisidine (2.0 g, 16.2 mmol) in chloroform. After 0.5 h, the mixture was poured into EtOAc and 1 N NaOH. The organic layer was washed with 1 N NaOH (1×), water (1×), dried over potassium carbonate, and concentrated. The residue was purified by recrystallization (EtOAc:hexanes) yielding 2.56 g (60%) of the title compound.
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