Nitrogen → HCID 22139416, compound

Participants

Reaction Conditions

Reaction Steps

2-Chloro-6-morpholin-4-yl-pyran-4-one (3)(215 mg, 1 mmol), 6-(4,4,5,5-Tetramethyl-[1,3,2]dioxaborolan-2-yl)-11H-dibenzo[b,f]thiepin-10-one (352 mg, 1 mmol), and ground potassium carbonate (276 mg, 2 mmol) were suspended in 1,4-dioxane (10 ml) and degassed for 5 minutes. Pd(PPh3)4 (57 mg, 0.05 mmol) was then added and the reaction mixture was then heated at 90° C. for 4hours under a vigorous stirring and a N2 atmosphere. The solvent was removed in vaccuo and the residue was then suspended in water (100 ml). The organics were extracted with dichloromethane (3×100 ml), combined, washed with saturated brine and dried over sodium sulphate. The solvent was removed in vaccuo and the residue was purified by column chromatography (silica; ethyl acetate:ethanol; 9:1) to give the title compound as a pale brown solid (0.12 g, 29%). 1HNMR (300 MHz, DMSO-d6): δH=3.40 (4H, t), 3.70 (4H, t), 4.43 (2H, s), 5.55 (1H, d), 6.29 (1H, d), 7.25–7.55 (5H, m), 7.78–7.81 (1H, m), 8.20–8.22 (1H, m); m/z (LC-MS, ESP), RT=4.12 min, (M++1)=406.

Provenance & Evidence