2-Fluoro-4-nitrophenol → 4-(2-Fluoro-4-nitrophenoxy)pyrrolo[2,1-f][1,2,4]triazine

Participants

Reaction Steps

4-Chloropyrrolo[2,1-f][1,2,4]triazine (4.1 g, 27 mmol), 2-fluoro-4-nitrophenol (5.0 g, 32 mmol), and potassium carbonate (7.4 g, 53 mmol) in 100 mL of dimethylformamide was stirred at 60° C. for 15 h. After cooling to room temperature, the reaction mixture was filtered through a plug of silica gel with EtOAc. The filtrate was concentrated in vacuo and the resulting crude product was purified by flash chromatography on silica gel (SiO2, EtOAc/Hexane 1:4) to give the title compound (4.25 g, 58%) as a white solid. 1H NMR (CDCl3) δ 8.09 (m, 2H), 7.88 (s, 1H), 7.77 (dd, 1H, J=2.6, 1.2 Hz), 7.46 (t, 1H, J=7.6 Hz), 6.98 (dd, 1H, J=4.6, 1.4 Hz), 6.84 (dd, 1H, J=4.5, 2.6 Hz); 13C NMR (CDCl3) δ 160.6, 154.3 (J=254 Hz), 146.5, 145.8, 144.8 (J=12.9 Hz), 125.0, 121.7, 120.7, 114.5, 113.9, 113.6 (J=23.2 Hz), 103.6.

Provenance & Evidence