Cl.[C:2]([C:6]1[CH:10]=[C:9]([NH2:11])[N:8]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([N+:18]([O-:20])=[O:19])[CH:13]=2)[N:7]=1)([CH3:5])([CH3:4])[CH3:3].N1C=CC=CC=1.[C:27](Cl)([O:29][CH2:30][C:31]([Cl:34])([Cl:33])[Cl:32])=[O:28]>C(Cl)Cl>[C:2]([C:6]1[CH:10]=[C:9]([NH:11][C:27](=[O:28])[O:29][CH2:30][C:31]([Cl:34])([Cl:33])[Cl:32])[N:8]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([N+:18]([O-:20])=[O:19])[CH:13]=2)[N:7]=1)([CH3:5])([CH3:3])[CH3:4]To a stirring suspension of 3-t-butyl-1-(3-nitrophenyl)-1H-pyrazol-5-amine hydrochloride (0.500 g, 1.685 mmol, 1.00 eq) and pyridine (0.412 ml, 5.05 mmol, 3.00 eq) in CH2Cl2 (17 ml) at 22° C. was added Troc-Cl (0.244 ml, 1.769 mmol, 1.05 eq). The reaction was stirred overnight at RT. The completed reaction was diluted with CH2Cl2 and washed with 3M HCl (2×). The combined aqueous were extracted with CH2Cl2 (1×). The combined organics were washed with H2O (2×), brine (1×), dried (Na2SO4), filtered ad evaporated. The crude product was purified by flash column chromatography (100% hexanes to 30% EtOAc/hexanes) to afford 2,2,2-trichloroethyl 3-t-butyl-1-(3-nitrophenyl)-1H-pyrazol-5-ylcarbamate (0.67 g, 91% yield) as an oil.
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