Sodium ethoxide → HCID 66779074, compound

Participants

Reaction Steps

To a dry 5 mL sealed tube with stirbar was added 1-(4-fluorophenyl)-4-iodo-2-oxo-N-{4-[(2-phenylfuro[3,2-b]pyridin-7-yl)oxy]phenyl}-1,2-dihydropyridine-3-carboxamide (46.30 mg; 0.07 mmol; 1.00 eq.) and the vial was sealed and flushed with N2. To the vial was added dry THF (1.00 ml) via syringe and then sodium ethoxide (0.04 ml; 0.09 mmol; 1.30 eq.) (21% solution in ethanol) was slowly added via syringe and the reaction mixture was stirred at room temperature for 1 h. The solution was concentrated, taken up in EtOAc and washed with sat. aq. NaHCO3. The organic layer was collected, extracting aqueous layer with EtOAc (3×). Combined organic layers were dried (Na2SO4) and concentrated on rotary evaporator to afford the title compound as a beige solid (40 mg, 100%). (HPLC (method F): 99%, RT: 6.08 min); 1H NMR (400 MHz, DMSO-d6) δ [ppm] 10.41 (s, 1H), 8.34 (d, J=5.5, 1H), 7.97-7.90 (m, 2H), 7.86 (d, J=7.8, 1H), 7.83-7.77 (m, 2H), 7.69 (s, 1H), 7.58-7.50 (m, 2H), 7.50-7.43 (m, 3H), 7.41-7.35 (m, 2H), 7.34-7.27 (m, 2H), 6.71 (d, J=5.5, 1H), 6.52 (d, J=7.9, 1H), 4.26 (q, J=7.0, 2H), 1.30 (t, J=7.0, 3H); MS (m/z) 562 [M+H]+, RT: 3.5 min.

Provenance & Evidence