[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6](=[O:19])[C:7]([CH3:18])=[CH:8][N:9]2[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[CH:4][CH:3]=1.C1C(=O)N([Br:27])C(=O)C1.CC(N=NC(C#N)(C)C)(C#N)C>C(Cl)(Cl)(Cl)Cl>[Br:27][CH2:18][C:7]1[C:6](=[O:19])[C:5]2[C:10](=[CH:11][C:2]([Cl:1])=[CH:3][CH:4]=2)[N:9]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:8]=1In a 50 mL round-bottomed flask, 7-chloro-3-methyl-1-phenyl-1H-quinolin-4-one (0.142 g, 0.526 mmol), NBS (103 mg, 0.579 mol) and AIBN (13.0 mg, 0.079 mmol) were combined with carbon tetrachloride (3.5 mL) to give a colorless solution. The reaction mixture was heated at 115° C. for 1 h. The reaction mixture was cooled to room temp and then cooled to 0° C. The mixture was filtered to remove succinimide and the filtrate was concentrated. The crude product was used in the next step without further purification.
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