Cl[C:2](=[O:8])[C:3]([O:5][CH2:6][CH3:7])=[O:4].[NH2:9][C:10]1[CH:15]=[CH:14][C:13]([Br:16])=[CH:12][C:11]=1[C:17](=[O:19])[CH3:18].N1C=CC=CC=1.O>ClCCl>[CH2:6]([O:5][C:3](=[O:4])[C:2]([NH:9][C:10]1[CH:15]=[CH:14][C:13]([Br:16])=[CH:12][C:11]=1[C:17](=[O:19])[CH3:18])=[O:8])[CH3:7]
Ethyl chlorooxoacetate (352.7 μL, 3.15 mmol) was added to 1-(2-amino-5-bromophenyl)ethanone (519.8 mg, 2.43 mmol, Example 34c) and pyridine (589.1 μL, 7.28 mmol) in dichloromethane (8 mL) at 0° C. under argon and the reaction was allowed to warm to room temperature and stirred for 17 hours. Water was added, and the solution was extracted with diethyl ether. The organic layer was washed with 10% citric acid, then saturated sodium bicarbonate, dried over anhydrous magnesium sulfate, filtered, and concentrated. The residue was purified by silica gel chromatography eluting with 1:4 ethyl acetate:hexanes to give 648.7 mg (85%) of ethyl[(2-acetyl-4-bromophenyl)amino](oxo)acetate as a solid. 1H NMR (400 MHz, d6-DMSO): δ 12.61 (s, 1H), 8.47 (d, J=9 Hz, 1H), 8.26 (d, J=2 Hz, 1H), 7.88 (dd, J=9, 2 Hz, 1H), 4.31 (q, J=7 Hz, 2H), 2.69 (s, 3H), 1.32 (t, J=7 Hz, 3H). ESI-LCMS m/z 314 (M+H)+.
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