[F:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6](=[O:20])[C:7]([CH3:19])=[CH:8][N:9]2[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[F:18])=[CH:4][CH:3]=1.BrN1C(=O)CCC1=O.N(C(C)(CC(C)C)C#N)=NC(C)(CC(C)C)C#N.[N-:47]=[N+:48]=[N-:49].[Na+]>C(Cl)(Cl)(Cl)Cl>[N:47]([CH2:19][C:7]1[C:6](=[O:20])[C:5]2[C:10](=[CH:11][C:2]([F:1])=[CH:3][CH:4]=2)[N:9]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[F:18])[CH:8]=1)=[N+:48]=[N-:49]
In a 50 mL round bottom flask, 7-fluoro-1-(2-fluoro-phenyl)-3-methyl-1H-quinolin-4-one (1.20 g, 4.42 mmol), N-bromosuccinimide (0.787 g, 4.42 mmol) and V65 [2,2′-azobis(2,4-dimethylvaleronitrile)](0.33 g, 1.33 mmol) were combined with carbon tetrachloride (35.0 mL). The reaction mixture was heated to reflux for 5 hr. The reaction was concentrated to dryness and the crude (containing 3-bromomethyl-7-fluoro-1-(2-fluoro-phenyl)-1H-quinolin-4-one) was redissolved in DMF (10.0 mL). To this reaction mixture was added sodium azide (1.44 g, 22.1 mmol) and the reaction was stirred at room temperature overnight. The reaction was partitioned between ethyl acetate and water and the organic layer was washed with saturated aqueous sodium bicarbonate solution. The organic layer was evaporated to dryness and purified by flash chromatography using 40% ethyl acetate-hexanes to afford 3-azidomethyl-7-fluoro-1-(2-fluoro-phenyl)-1H-quinolin-4-one (740 mg, 53.6%).
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