[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:10]2[CH:11]=[C:12]3[C:17](=[CH:18][CH:19]=2)[N:16]=[C:15](Br)[CH:14]=[C:13]3[Br:21])=[O:9])=[CH:4][CH:3]=1.[OH2:22]>C1(C)C=CC=CC=1.CCOC(C)=O>[Br:21][C:13]1[C:12]2[C:17](=[CH:18][CH:19]=[C:10]([C:8]([C:5]3[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=3)=[O:9])[CH:11]=2)[N:16]=[C:15]([O:22][C:5]([CH3:8])([CH3:6])[CH3:4])[CH:14]=1A mixture of (4-chlorophenyl)(2,4-dibromoquinolin-6-yl)methanone (5 g) and KOBut (1.1 eq. 12.93 mmol) in dry toluene (60 mL) was heated at 70° C. for 2 hr. and then cooled to room temperature. The reaction was diluted with EtOAc and water. The aqueous layer was extracted with ethyl acetate. The organics were combined and then washed with water, concentrated and subjected to chromatography (5-15% EtOAc/hexanes silica column) to yield (4-bromo-2-(tert-butoxy)quinolin-6-yl)(4-chlorophenyl)methanone.
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