Nitrogen → KU-55933

Participants

Reaction Conditions

Reaction Steps

2-Chloro-6-morpholin-4-yl-pyran-4-one (3) (863 mg, 4 mmol), thianthrene-1-boronic acid (1.145 g, 4.4 mmol), and ground potassium carbonate (1.105 g, 8 mmol) were suspended in dioxane (10 ml) and degassed (sonication for 5 minutes then saturated with N2). Pd(PPh3)4 (231 mg, 0.2 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 was removed in vacuo and the residue was then suspended in water 50 ml) and extracted with ethyl acetate (3×100 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 (70 mg, 4%). 1H-NMR (300 MHz, DMSO-d6): δH=3.44 (4H, t, J 5 Hz); 3.76 (4H, t, J 5 Hz); 5.57 (1H, d, J 2 Hz); 6.30 (1H, d, J 2 Hz); 7.43 (2H, m); 7.53 (1H, t, 8 Hz); 7.66 (3H, m); 8.49 (1H, dd, J land 8 Hz). m/z (LC-MS, ESP): 396 (M++1).

Provenance & Evidence