Br[CH2:2][C:3]1[C:12](=[O:13])[C:11]2[C:6](=[CH:7][C:8]([Cl:14])=[CH:9][CH:10]=2)[N:5]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[Cl:21])[CH:4]=1.[N-:22]=[N+:23]=[N-:24].[Na+].CN(C=O)C>C(OCC)(=O)C>[N:22]([CH2:2][C:3]1[C:12](=[O:13])[C:11]2[C:6](=[CH:7][C:8]([Cl:14])=[CH:9][CH:10]=2)[N:5]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[Cl:21])[CH:4]=1)=[N+:23]=[N-:24]To a 25 mL round-bottom flask containing the crude 3-bromomethyl-7-chloro-1-(2-chloro-phenyl)-1H-quinolin-4-one (410 mg, 1.07 mmol) was added sodium azide (83.5 mg, 1.28 mmol) and DMF (9 mL). The reaction mixture was stirred overnight at room temperature. The mixture was diluted with ethyl acetate (100 mL) and washed with brine (100 mL). The organic layer was dried over magnesium sulfate, filtered, and concentrated. The crude was purified by flash chromatography (silica gel, 24 g, 0-50% ethyl acetate in hexanes) to yield 3-azidomethyl-7-chloro-1-(2-chloro-phenyl)-1H-quinolin-4-one (215 mg, 58%) as a light yellow solid. 1H NMR (DMSO-d6) δ ppm 8.17-8.36 (m, 2H) 7.83 (ddd, J=9.8, 7.9, 1.7 Hz, 2H) 7.68 (ddd, J=9.8, 7.8, 1.6 Hz, 2H) 7.48 (dd, J=8.7, 1.8 Hz, 1H) 6.70 (d, J=1.8 Hz, 1H) 4.09-4.44 (m, 2H). MS calcd. for C16H10Cl2N4O [(M+H)+] 346.0, obsd. 345.0.
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