N#N.[F:3][C:4]([C:7]1[O:11][C:10]([CH2:12][N:13]2[CH:17]=[C:16]([N+:18]([O-])=O)[CH:15]=[N:14]2)=[CH:9][CH:8]=1)([F:6])[CH3:5].[NH4+].[Cl-]>CCO.O.[Fe]>[F:6][C:4]([C:7]1[O:11][C:10]([CH2:12][N:13]2[CH:17]=[C:16]([NH2:18])[CH:15]=[N:14]2)=[CH:9][CH:8]=1)([F:3])[CH3:5]In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), a mixture of 1-[5-(1,1-difluoro-ethyl)-furan-2-ylmethyl]-4-nitro-1H-pyrazole (234 mg, 0.91 mmol), iron powder (154 mg, 2.73 mmol) and NH4Cl (246 mg, 4.55 mmol) in a mixture of EtOH (4.0 mL) and water (2.0 mL) was stirred at 75° C. for 1 h. The reaction mixture was filtered while hot and concentrated under reduced pressure. CH2Cl2 (20 mL) was added followed by 1M NaOH (20 mL). The aq. layer was extracted with CH2Cl2 (2×20 mL). The combined org. extracts were dried over MgSO4, filtered, and the solvents were removed under reduced pressure to give the title compound as an orange oil. LC-MS-conditions 02: tR=0.65 min; [M+AcCN+H]+=269.07.
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