[NH2:1][C:2]1[N:6]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[N:5]=[C:4]([O:14][CH:15]([CH3:17])[CH3:16])[CH:3]=1.[Li+].C[Si]([N-][Si](C)(C)C)(C)C.[F:28][C:29]1[N:36]=[C:35](F)[C:34]([F:38])=[CH:33][C:30]=1[C:31]#[N:32]>C1COCC1>[C:31]([C:30]1[CH:33]=[C:34]([F:38])[C:35]([NH:1][C:2]2[N:6]([C:7]([O:9][C:10]([CH3:11])([CH3:12])[CH3:13])=[O:8])[N:5]=[C:4]([O:14][CH:15]([CH3:17])[CH3:16])[CH:3]=2)=[N:36][C:29]=1[F:28])#[N:32]A solution of tert-butyl 5-amino-3-isopropoxy-1H-pyrazole-1-carboxylate (Method 78, 4.0 g, 16.4 mmol) in THF (45 ml) was cooled to −78° C. A 1.0M THF solution of LiHMDS (2.61 g, 15.6 mmol) was added dropwise and the reaction was stirred at −78° C. for 30 minutes. A −78° C. solution of 2,5,6-trifluoronicotinonitrile (1.3 g, 8.2 mmol) in THF (20 ml) was added dropwise via cannula to the above anion solution. Upon completion of the addition, the resulting reaction was allowed to stir for 10 minutes at −78° C., and was then quenched with water (100 ml). The reaction was allowed to warm to room temperature, extracted with DCM (3×100 ml), dried (Na2SO4), filtered, and then concentrated to give the title compound (95% conversion by LCMS) which was used without further purification. MS: Calcd.: 379. Found: [M+H]+ 380.
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