Nitrogen → HCID 22139439, compound

Participants

Reaction Conditions

Reaction Steps

2-Chloro-6-morpholin-4-yl-pyran-4-one (3)(740 mg, 3.43 mmol), dibenzothiophene-1-boronic acid (860 mg, 3.77 mmol), and ground potassium carbonate (964 mg, 6.86 mmol) were suspended in dioxane (10 ml) and degassed (sonication for 5 minutes then saturated with N2). Pd(PPh3)4 (200 mg, 0.17 mmol) was then added and the reaction mixture was then heated at 90° C. for 24 hours under a vigorous stirring and a N2 atmosphere. The solvent were removed in vacuo and the residue was then suspended in water (50 ml) and extracted with ethyl acetate (3×50 ml). The organics were combined, washed with saturated brine and dried over sodium sulphate. The solvent was removed in vacuo and the residue was purified by column chromatography (silica; ethyl acetate:ethanol; 9:1) to give the title compound as a white solid (80 mg, 6%). 1H-NMR (300 MHz, DMSO-d6): δH=3.49 (4H, t, J 5 Hz); 3.76 (4H, t, J 5 Hz); 5.53 (1H, d, J 2 Hz); 6.63 (1H, d, J 2 Hz); 7.59 (2H, m); 7.69 (1H, t, J 8 Hz); 7.96 (1H, dd, J 1 and 7.5 Hz); 8.11 (1H, m); 8.47 (1H, m); 8.57 (1H, dd, J 1 and 8 Hz). m/z (LC-MS, ESP): 364 (M++1).

Provenance & Evidence