Potassium Carbonate → 2-Morpholin-4-yl-8-(1-nitro-dibenzofuran-4-yl)-1H-quinolin-4-one

Participants

Reaction Steps

In a Schlenk tube, 1-nitro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) dibenzofuran (12) (500 mg, 1.47 mmol) and potassium carbonate (480 mg, 3.69 mmol) were solubilised in dioxane (10 mL) and degassed. Concurrently, 8-bromo-2-morpholin-4-yl-1H-quinolin-4-one (21) (380 mg, 1.23 mmol) and Pd(PPh3)4 (71 mg, 0.06 mmol) were solubilised in dioxane (10 mL) and degassed. The solutions were mixed together in a microwave vessel, which was placed into the microwave reactor at 180° C. for 30 min. Upon cooling, DCM (20 mL) was added. The solution was washed with water (20 mL), then dried on magnesium sulfate and evaporated. The residue was purified by flash chromatography using AcOEt/EP (8:2) as eluant to furnish the title compound (303 mg, 0.74 mmol, 60%) as a yellow solid: Rf=0.67 (AcOEt); mp: 247° C.; λmax (EtOH)/nm 251; IR (cm−1) 3421, 2852, 2360, 2333, 1614, 1573, 1500, 1435, 1429, 1348, 1309, 1233, 1199, 1152, 1124, 1039, 991, 917, 866, 823; 1H NMR, (300 MHz, CDCl3) δ 3.04 (4H, m, 2×CH2—N-morpholine), 3.54 (4H, m, 2×CH2—O-morpholine), 5.92 (1H, s, H-3), 7.19-7.45 (2H, m), 7.51-7.58 (2H, m), 7.65-7.70 (2H, m), 8.31 (2H, m), 8.67 (1H, d, J=7 Hz); MS (EI) m/z 442.29 M+; HRMS calcd for C25H20N3O5 [M+H]+ 442.1397, found 442.1398.

Provenance & Evidence