[Cl:1][C:2]1[N:3]=[CH:4][N:5]([C:7]2[C:12]([O:13][CH3:14])=[CH:11][C:10]([N+:15]([O-])=O)=[CH:9][C:8]=2[F:18])[CH:6]=1.[Cl-].[NH4+]>[Zn].CO>[Cl:1][C:2]1[N:3]=[CH:4][N:5]([C:7]2[C:12]([O:13][CH3:14])=[CH:11][C:10]([NH2:15])=[CH:9][C:8]=2[F:18])[CH:6]=1Step M (6): A mixture of 4-chloro-1-(2-fluoro-6-methoxy-4-nitrophenyl)-1H-imidazole (60 mg, 0.22 mmol), zinc dust (70 mg, 1.1 mmol), ammonium chloride (58 mg, 1.1 mmol), and methanol (5 mL) was heated at 110° C. for 16 h. The reaction mixture was quenched with 1 N HCl. The organic layer was washed with brine, dried over sodium sulfate, filtered, and concentrated in vacuo. The residue was purified using silica gel column chromatography (15% EtOAc/hexane) to afford 4-(4-chloro-1H-imidazol-1-yl)-3-fluoro-5-methoxyaniline (20 mg, 38% yield). LC-MS (M+H)+ 242.0. 1H NMR (400 MHz, DMSO-d6) δ ppm 7.59 (s, 1 H) 7.28 (s, 1 H) 6.96 (s, 1 H), 6.08 (d, J=12.2 Hz, 1 H) 5.83 (s, 2 H) 3.67 (s, 3 H).
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