[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[N:9]1[C:13]([NH:14][CH2:15][CH3:16])=[CH:12][CH:11]=[N:10]1.[N:17](OCCC(C)C)=[O:18]>CCOC(C)=O.CCO.Cl.CC(O)C>[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[N:9]1[C:13]([NH:14][CH2:15][CH3:16])=[C:12]([N:17]=[O:18])[CH:11]=[N:10]1A solution of 1-(2,4-difluorophenyl)-N-ethyl-1H-pyrazol-5-amine (1.15 g, 5.16 mmol) in 4.0 mL of EtOAc, 2.0 mL of EtOH and 4.0 mL of 5-6 N HCl in 2-propanol was cooled in an ice/brine bath and treated with isoamyl nitrite (0.70 mL, 5.28 mmol) drop wise. After stirring at this temperature for 15 min, the reaction was quenched by the addition of 28-30% NH4OH solution and EtOAc, forming a deep blue solution. The EtOAc layer was separated, washed with brine, dried and concentrated to afford the title compound as a brown crystalline solid. MS (ES+): 253.1 (M+H)+.
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