Water → HCID 86655254, compound

Participants

Reaction Steps

Sodium hydride (0.124 g, 5.18 mmol) was added to a chilled (0° C.) solution of 4-fluoro-2-(trifluoromethyl)aniline (0.464 g, 2.59 mmol) in THF (1 mL) and stirred for 30 min. 2,6-Dichloro-3-nitropyridine (0.500 g, 2.59 mmol) was then added and the reaction mixture stirred at 80° C. for 18 h. Water was added to quench excess sodium hydride and volatile solvents were removed under reduced pressure. The product was then extracted into DCM, solvent removed under reduced pressure, and the residue purified by preparative HPLC to give the title compound (0.624 g). LCMS m/z=336.0 [M+H]+; 1H NMR (400 MHz, CDCl3) δ ppm 6.87 (d, J=8.6 Hz, 1H), 7.34 (td, J1=8.4 Hz, J2=3.0 Hz, 1H), 7.43 (dd, J1=8.4 Hz, J2=3.0 Hz, 1H), 7.94 (dd, J1=9.0 Hz, J2=5.0 Hz, 1H), 8.49 (d, J=8.6 Hz, 1H), 10.26 (br s, 1H).

Provenance & Evidence