Dichloromethane → HCID 68285193, compound

Participants

Reaction Steps

5-bromo-4-(3-nitrophenyl)-2-(tetrahydro-2H-pyran-4-yl)-1,3-thiazole (140 mg, 0.379 mmol) was dissolved into a mixture of degassed dioxane (8 mL) and water (1.6 mL). 2-(4-pyridyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (78 mg, 0.379 mmol, 1 eq.), cesium carbonate (370 mg, 1.137 mmol, 3 eq.) and PdCl2(dppf)2.CH2Cl2 (31 mg, 0.0379 mmol, 0.1 eq) were subsequently added to the solution. The mixture so obtained was stirred and heated to reflux under argon atmosphere for 5 h. After cooling, the suspension was filtered through a celite pad, and evaporated to dryness. The crude was re-dissolved in ethyl acetate and washed twice with brine. The organic layer was dried over sodium sulphate and evaporated to dryness. The solid material so obtained was then purified by silica gel column chromatography eluting with ethyl acetate/Hex (6/4) yielding the title compound (98 mg, 70%).

Provenance & Evidence