[Br:1][C:2]1[C:7]([F:8])=[CH:6][CH:5]=[C:4]([N+:9]([O-])=O)[C:3]=1[NH:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=1.[Cl-].[NH4+]>CO.O.[Fe]>[Br:1][C:2]1[C:7]([F:8])=[CH:6][CH:5]=[C:4]([NH2:9])[C:3]=1[NH:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=1
(2-Bromo-3-fluoro-6-nitro-phenyl)-pyridin-2-yl-amine (3.68 g, 11.8 mmol), iron powder (2.63 g, 47.2 mmol), and ammonium chloride (3.63 g, 70.7 mmol) in methanol (40 mL) and water (15 mL) were heated at 90° C. for 1.5 h. The reaction mixture was filtered and the filtrate concentrated in vacuo. The residue was dissolved in water and extracted with EtOAc (3×40 mL). The combined organic extracts were washed with brine, dried (MgSO4) and concentrated in vacuo. The resultant residue was subjected to flash chromatography (SiO2, eluting with 0-10% methanol in EtOAc) to yield the title compound as a white solid (2.5 g, 75%). 1H NMR 400 MHz δ (CDCl3): 8.23-8.17 (1H, m), 7.48 (1H, ddd, J=8.4, 7.3, 1.9 Hz), 6.94 (1H, dd, J=8.8, 7.9 Hz), 6.77 (1H, ddd, J=7.2, 5.0, 1.0 Hz), 6.73 (1H, dd, J=8.8, 5.0 Hz), 6.31 (1H, dt, J=8.3, 1.0 Hz), 6.10 (1H, br s), 3.94 (2H, br s).
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