[OH-:1].[K+].[F:3][C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][C:8](=[O:13])[C:7]2=O.[Br:15][C:16]1[CH:17]=[C:18]([C:22](=O)[CH2:23][CH3:24])[CH:19]=[CH:20][CH:21]=1.Cl>C(O)C>[Br:15][C:16]1[CH:17]=[C:18]([C:22]2[C:23]([CH3:24])=[C:7]([C:8]([OH:13])=[O:1])[C:6]3[C:10](=[CH:11][CH:12]=[C:4]([F:3])[CH:5]=3)[N:9]=2)[CH:19]=[CH:20][CH:21]=1Potassium hydroxide (19.98 g, 356 mmol) was added to a suspension of 5-fluoro-1H-indole-2,3-dione (10 g, 59.4 mmol) in ethanol (96 mL). 1-(3-Bromophenyl)-1-propanone (13.91 g, 65.3 mmol) was added and the mixture was heated to reflux for 1 h. The reaction mixture was cooled to room temperature and acidified to pH 3 with concentrated HCl. The solid was collected by filtration, washed with water, and dried to afford 2-(3-bromophenyl)-6-fluoro-3-methyl-4-quinolinecarboxylic acid (20.9 g, 98% yield). This material was used without further purification. MS (m/z) 360.0 (M+H+).
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