[I:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)=[CH:7][C:8]([NH2:12])=[N:9]2)=[CH:4][CH:3]=1.Br[CH2:20][C:21](=O)[C:22]([O:24][CH2:25][CH3:26])=[O:23].C(=O)(O)[O-].[Na+]>CCO>[CH2:25]([O:24][C:22]([C:21]1[N:12]=[C:8]2[CH:7]=[C:6]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[C:5]3[C:10](=[CH:11][C:2]([I:1])=[CH:3][CH:4]=3)[N:9]2[CH:20]=1)=[O:23])[CH3:26]7-Iodo-4-phenyl-quinolin-2-ylamine (100 mg, 0.29 mmol), ethyl bromopyruvate (0.05 mL, 0.43 mmol), and sodium bicarbonate (22 mg, 0.58 mmol) were dissolved in EtOH (2 mL) and heated to 80° C. for 3 hours. The mixture was concentrated and purified by silica gel chromatography (30% EtOAc in hexanes) to give the desired product, 1v.
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