Nitrogen → HCID 22139450, compound

Participants

Reaction Conditions

Reaction Steps

2-Chloro-6-morpholin-4-yl-pyran-4-one (3)(1.12 g, 5.2 mmol), 2-(10,11-Dihydro-dibenzo[b,f]thiepin-4-yl)-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane (880 mg, 2.6 mmol), and ground potassium carbonate (720 mg, 5.2 mmol) were suspended in 1,4-dioxane (10 ml) and degassed for 5 minutes. bis(tri-t-butylphosphine)palladium (66 mg, 0.13 mmol) was then added and the reaction mixture was then heated at 90° C. for 4 hours 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 a pale brown solid (50 mg, 5%). 1HNMR (300 MHz, DMSO-d6): δH=3.24–3.32 (6H, m), 3.44 (2H, t), 3.66 (4H, t), 5.50 (1H, d), 6.10 (1H, d), 7.08–7.51 (7H, m); m/z (LC-MS, ESP), RT=4.48 min, (M++1)=392.

Provenance & Evidence