[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:11])[CH2:9][CH3:10])=[C:4]([NH:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[F:19])[CH:3]=1.[C:20](Cl)(=O)C(Cl)=O>CN(C=O)C>[F:1][C:2]1[CH:3]=[C:4]2[C:5]([C:8](=[O:11])[C:9]([CH3:20])=[CH:10][N:12]2[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[F:19])=[CH:6][CH:7]=1In a 250 mL round bottom flask, 1-[4-fluoro-2-(2-fluoro-phenylamino)-phenyl]-propan-1-one (3.05 g, 11.7 mmol) was added to DMF (4.3 mL) at 0° C. Oxalyl chloride (8.18 mL, 96.7 mmol) was added slowly and the reaction mixture stirred at 0° C. The mixture was then warmed up to room temperature and stirred for 1.5 hr. The mixture was concentrated to dryness and the crude redissolved in toluene (80 mL). The reaction mixture was heated at 115° C. for 24 hr. The mixture was concentrated to dryness and triturated from methanol to afford 7-fluoro-1-(2-fluoro-phenyl)-3-methyl-1H-quinolin-4-one (1.20 g, 37.8%) as a white solid.
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