[NH2:1][C:2]1[N:6]([C:7]2[CH:12]=[CH:11][C:10]([F:13])=[CH:9][CH:8]=2)[N:5]=[CH:4][C:3]=1[C:14]#N.[H][H].[OH-:18].[Na+]>[Ni].O.C(O)(=O)C>[NH2:1][C:2]1[N:6]([C:7]2[CH:12]=[CH:11][C:10]([F:13])=[CH:9][CH:8]=2)[N:5]=[CH:4][C:3]=1[CH:14]=[O:18]5-Amino-1-(4-fluorophenyl)-1H-pyrazole-4-carbonitrile (110, R1=4-Fluorophenyl) (56.2 g, 278 mmol), acetic acid (270 mL), water (75 mL) and Raney 2400 Nickel slurry in water (15 g, 278 mmol) was shaken under about 30 psi hydrogen at about 20°-25° C. for about 8 h. The mixture was filtered through a pad of Celite®. The contents of the reaction vessel were transferred with acetic acid (150 mL) and the pad was washed with an additional portion of acetic acid (200 mL). The filtrate was concentrated under reduced pressure to give a slurry. Water (300 mL) was added then the mixture was stirred for about 15 min. The mixture was cooled in an ice/water bath then basified with 5 N aq. NaOH. After stirring for about 20 min in the ice/water bath the solids were collected by filtration and washed with water (100 mL).
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