[H-].[Na+].[Br:3][C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][C:12]=1[F:13])[NH:9][CH:8]=[CH:7]2.Br[CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17]>C1COCC1>[CH2:19]([O:18][C:16](=[O:17])[CH2:15][N:9]1[C:10]2[C:6](=[CH:5][C:4]([Br:3])=[C:12]([F:13])[CH:11]=2)[CH:7]=[CH:8]1)[CH3:20]NaH (81 mg, 3.21 mmol) was added to a 0° C. solution of 5-bromo-6-fluoro-1H-indole (0.343 g, 1.60 mmol) in THF (16 mL). The reaction mixture was stirred at 0° C. for 15 min, then ethyl bromoacetate (0.535 mL, 4.81 mmol) was added. The reaction was stirred at rt for 1 h, then partitioned between water and EtOAc. The aqueous layer was extracted with EtOAc and the combined organic layers were washed with brine, dried (Na2SO4), filtered, and concentrated. The crude product was used in the next step without further purification.
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