Under hydrogen atmosphere, 1-(4-nitrophenyl)-3,5-bis(trifluoromethyl)-1H-pyrazole (4.4 g, 13.5 mmol) was dissolved in EtOAc (44 mL) and Pd/C (1.3 g) was added. The reaction mixture was stirred at room temperature for 2 hours. Upon completion of the reaction, the mixture was vacuum filtered through a diatomaceous earth pad and the filter cake was washed with EtOAc. The filtrate was concentrated under reduced pressure to afford 4-(3,5-bis(trifluoromethyl)-1H-pyrazol-1-yl)-aniline (compound 13) as a light yellow solid (3.75 g, 12.7 mmol, 94% yield). The product was characterized by 1H-NMR (300 MHz, CDCl3) and mass spectrometry (MS): 1H-NMR δ 7.22 (d, J=8.5 Hz, 2H), 7.00 (s, 1H), 6.72 (d, J=8.5 Hz, 2H); MS m/z: [M+H]+ 296.
