[C:1]([C:3]1[CH:8]=[C:7]([C:9]2[N:13]([C:14]3[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=3)[N:12]=[C:11]([CH3:21])[CH:10]=2)[CH:6]=[CH:5][N:4]=1)#[N:2].OO.C(=O)([O-])[O-:25].[K+].[K+].O>CS(C)=O>[F:20][C:17]1[CH:18]=[CH:19][C:14]([N:13]2[C:9]([C:7]3[CH:6]=[CH:5][N:4]=[C:3]([C:1]([NH2:2])=[O:25])[CH:8]=3)=[CH:10][C:11]([CH3:21])=[N:12]2)=[CH:15][CH:16]=1To a solution of 2-cyano-4-[1-(4-fluorophenyl)-3-methyl-1H-pyrazol-5-yl]pyridine (Example 32; 1.0 g, 0.0036 mol) in 25 mL of DMSO was added hydrogen peroxide (0.43 mL, 0.0036 mol) and potassium carbonate (0.072 g, 0.00051 mol) at zero degrees C. The reaction mixture was warmed up to room temperature over 1 hour. Water was added and the mixture was stirred for 0.5 hours. The resulting precipitate was collected by filtration to give 0.95 g (89% yield) of product as a pale yellow solid: mp: 168-170° C.; Anal. Calc'd. for C16H13FN4O: C, 64.86; H, 4.42; N, 18.91. Found: C, 64.48; H, 4.27; N, 18.80.
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