[Na].[Cl:2][C:3]1[N:4]=[C:5]2[C:9](=[CH:10][C:11]=1[Cl:12])[NH:8][C:7](=[O:13])[CH2:6]2.[S:14]1[CH:18]=[CH:17][CH:16]=[C:15]1[C:19](OCC)=[O:20].Cl>C(O)C>[Cl:2][C:3]1[N:4]=[C:5]2[C:9](=[CH:10][C:11]=1[Cl:12])[NH:8][C:7](=[O:13])[CH:6]2[C:19](=[O:20])[C:15]1[S:14][CH:18]=[CH:17][CH:16]=1Pellets of sodium metal (0.29 g, 12.6 mmol) were added to dry ethanol (10 mL) in a dry round-bottomed flask. When dissolution of the sodium was complete, solid 5,6-dichloro-4-azaoxindole (500 mg, 2.46 mmol) was added followed by ethyl 2-thiophenecarboxylate (0.67 mL. 5.0 mmol). The mixture was heated at reflux for one day under nitrogen. The mixture was cooled, poured into ice/water and acidified to pH 3 with 6N HCl solution. The title compound was collected by filtration and dried in vacuo to afford 607 mg (79%).
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