2-Nitroaniline → (2-Nitrophenyl)-{2,2,2-trifluoro-1-[1-(4-fluorophenyl)-1H-indazol-5-yl]ethyl}amine

Participants

Reaction Steps

To a solution of 134 mg (0.97 mmol) of 2-nitroaniline in 5 mL of dichloromethane was added 300 mg (0.97 mmol) of 2,2,2-trifluoro-1-[1-(4-fluorophenyl)-1H-indazol-5-yl]ethanone, 210 μL (2.9 mmol) of triethylamine, followed by 500 μL 0.5 mmol) of TiCl4. The mixture stirred for 20 hours and was then diluted with methanol followed by 40 mg (1.0 mmol) of sodium borohydride. After 1 hour, the mixture was diluted with 50 mL of 1N aqueous NaOH and extracted with EtOAc. The combined organic layers were washed with brine, dried over sodium sulfate, and concentrated in vacuo. The crude product was purified by Combiflash chromatography using EtOAc-hexanes (0-70% gradient) to afford 220 mg (53%) of the title compound as a yellow foam. MS m/z 431 (MH+).

Provenance & Evidence