Potassium Fluoride → HCID 59380851, compound

Participants

Reaction Steps

2-Chloro-3-phenyl-1,5-naphthyridine (3-5; 103 mg, 0.43 mmole), 4-formylphenylboronic acid (77 mg, 0.51 mmole), KF (82 mg, 1.4 mmole), and Pd(PtBu3)2 (11 mg, 0.02 mmole) were combined in dry dioxane (2.5 mL). The mixture was degassed (3× pump/N2) then heated to reflux. After 18 hr the mixture was cooled to RT. 4-Formylphenylboronic acid (77 mg, 0.51 mmole), KF (82 mg, L 1.4 mmole), and Pd(PtBu3)2 (11 mg, 0.02 mmole) were added. The mixture was degassed (3× pump/N2) then heated to reflux. After 6 hr the mixture was cooled, diluted with saturated NaHCO3, and extracted with CH2Cl2 (3×). The combined organic layers were dried (MgSO4), filtered, and concentrated. Flash column (20% EtOAc/CHCl3) gave the title compound (3-6) as a pale yellow gum: 1H-NMR (500 MHz, CDCl3) δ 10.03 (s, 1H), 9.05 (bs, 1H), 8.48 (m, 2H), 7.82 (dd, J=1.47 and 5.13 Hz, 2H), 7.71 (m, 1H), 7.63 (d, J=8.06 Hz, 2H), 7.36-7.27 (m, 5H).

Provenance & Evidence