CN[C@H]1CCCC[C@@H]1NC.P([O-])([O-])([O-])=O.[K+].[K+].[K+].I[C:20]1[CH:25]=[CH:24][C:23]([C:26]([F:29])([F:28])[F:27])=[CH:22][CH:21]=1.[NH:30]1[CH:34]=[CH:33][C:32]([C:35]([O:37][CH3:38])=[O:36])=[N:31]1>CCOC(C)=O.[Cu](I)I.C1(C)C=CC=CC=1>[F:27][C:26]([F:29])([F:28])[C:23]1[CH:24]=[CH:25][C:20]([N:30]2[CH:34]=[CH:33][C:32]([C:35]([O:37][CH3:38])=[O:36])=[N:31]2)=[CH:21][CH:22]=1A 30 mL pressure tube was charged with (1S,2S)—N1,N2-dimethylcyclohexane-1,2-diamine 61 (0.41 mL, 2.6 mmol), copper iodide (361 mg, 1.9 mmol), potassium phosphate (6.1 g, 29 mmol), 1-iodo-4-(trifluoromethyl)benzene 62 (3.2 g, 12 mmol), methyl 1H-pyrazole-3-carboxylate 60 (1.5 g, 12 mmol), and 15 mL of toluene. This mixture was heated at 110° C. for 16 h. After cooling to room temperature, the mixture was diluted with EtOAc and filtered. The filtrate was concentrated onto silica and purified by flash column chromatography on silica gel (0% to 3% MeOH in DCM) to give methyl 1-(4-(trifluoromethyl)phenyl)-1H-pyrazole-3-carboxylate 63.
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