Sodium Carbonate → HCID 21103206, compound

Participants

Reaction Steps

2-Chloro-3-phenyl-1,8-naphthyridine (Rani, H. S.; Mogilaiah, K.; Sreenivasulu, B. Indian J. Chem. Sect. B. 1996, 35, 106; 154 mg, 0.64 mmole), 4-formylphenylboronic acid (144 mg, 0.96 mmole), 2 M Na2CO3 (0.64 mL, 1.28 mmole), and Pd(PPh3)4 (37 mg, 0.03 mmole) were combined in dioxane (3 mL) in a sealed microwave vessel. The mixture was degassed (3× vacuum/N2) then microwave irridiated at 150° C. for 30 min. The mixture was diluted with H2O and extracted with EtOAc (3×). The combined organic layers were dried (MgSO4), filtered, and concentrated. Flash column (60% EtOAc/hexanes) gave the title compound as a yellow foam (10-1): 1H-NMR (500 MHz, CDCl3) δ 10.02 (s, 1 H), 9.19 (dd, J=1.95, 2.20 Hz, 1 H), 8.28 (dd, J=1.95, 6.35 Hz, 1 H), 8.26 (s, 1 H), 7.79 (d, J=8.30 Hz, 2 H), 7.73 (d, J=8.05 Hz, 2 H), 7.57 (m, 1H), 7.35 (m, 2H), 7.27 (m, 3 H).

Provenance & Evidence