[Cl:1][C:2]1[C:3]([O:15][CH:16]([C:21]2[CH:22]=[N:23][CH:24]=[CH:25][CH:26]=2)[C:17]([F:20])([F:19])[F:18])=[N:4][C:5]2[C:10]([N:11]=1)=[CH:9][C:8]([N+:12]([O-])=O)=[CH:7][CH:6]=2.[Cl-].[NH4+]>C(O)C.O.[Fe]>[Cl:1][C:2]1[C:3]([O:15][CH:16]([C:21]2[CH:22]=[N:23][CH:24]=[CH:25][CH:26]=2)[C:17]([F:19])([F:20])[F:18])=[N:4][C:5]2[C:10]([N:11]=1)=[CH:9][C:8]([NH2:12])=[CH:7][CH:6]=2In a mixed solvent of ethanol (19.5 mL) and water (9.75 mL) was dissolved 3-chloro-6-nitro-2-(2,2,2-trifluoro-1-(pyridin-3-yl)ethoxy)quinoxaline (975 mg, 2.53 mmol) obtained in Step 2. To the solution were added iron (0) (425 mg, 7.60 mmol) and ammonium chloride (68.0 mg, 1.27 mmol) and the mixture was stirred at 80° C. for 1 hour. The reaction mixture was filtered through Celite and the filtrate was extracted with ethyl acetate. Washing with saturated brine and drying over anhydrous magnesium sulfate were performed. After filtration, the solvent in the filtrate was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=1/0 to 0/1) to give 3-chloro-2-(2,2,2-trifluoro-1-(pyridin-3-yl)ethoxy) quinoxaline-6-amine (555 mg, 62% yield).
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