4-Aminophenol → 4-[(2-Phenylfuro[3,2-b]pyridin-7-yl)oxy]aniline

Beteiligte Stoffe

Reaktionsbedingungen

Reaktionsschritte

To a 10 mL sealed tube with stirbar was added 7-chloro-2-phenylfuro[3,2-b]pyridine (300.00 mg; 1.31 mmol; 1.00 eq.), 4-aminophenol (285.09 mg; 2.61 mmol; 2.00 eq.), and caesium carbonate (1 702.45 mg; 5.22 mmol; 4.00 eq.). The mixture was suspended in DMF (7.00 ml) and stirred at 125° C. overnight. The reaction mixture was cooled to room temperature and poured into 150 mL water. Filtered to collect precipitate, washing with water and hexane. The resulting crude material was purified by Biotage chromatography using a KP-NH column (10-50% EtOAc/Hex) to afford the title compound as a beige solid (216 mg, 55%). (HPLC (method F): 99%, RT: 4.73 min); 1H NMR (400 MHz, DMSO-d6) δ [ppm] 8.29 (d, J=5.5, 1H), 7.96 (d, J=7.2, 2H), 7.66 (s, 1H), 7.54 (t, J=7.4, 3H), 7.47 (t, J=7.3, 1H), 6.99 (d, J=8.7, 2H), 6.67 (d, J=8.7, 2H), 6.56 (d, J=5.5, 1H), 5.20 (s, 2H); MS (m/z) 303 [M+H]+, RT: 2.6 min.

Herkunft & Nachweise