Phenol → 2-Chloro-6-phenoxy-4-(4-phenoxyphenyl)nicotinonitrile

Beteiligte Stoffe

Reaktionsschritte

A mixture of 2,6-dichloro-4-(4-phenoxyphenyl)nicotinonitrile (51 mg, 0.149 mmol, from Step 2 of Example 8), phenol (15.47 mg, 0.164 mmol) and cesium carbonate (97 mg, 0.299 mmol) in DMSO (1.5 mL) was stirred at room temperature for 15 h. The mixture was diluted with ethyl acetate (60 mL), washed with water (2×5 mL), brine (5 mL), dried (MgSO4) and concentrated. Silica gel chromatography, eluting with 0% to 20% ethyl acetate in hexanes, gave 2-chloro-6-phenoxy-4-(4-phenoxyphenyl)nicotinonitrile as a white solid (60 mg, 75% yield). 1H NMR (500 MHz, CDCl3) δ ppm 7.52-7.73 (2H, m), 7.37-7.52 (4H, m), 7.25-7.36 (1H, m), 7.20-7.24 (1H, m), 7.08-7.18 (4H, m), 6.87 (1H, s); MS (ES+) m/z: 399 (M+H); LC retention time: 4.283 min (analytical HPLC Method A).

Herkunft & Nachweise