Potassium Carbonate → 5-(3,6-Dihydro-2H-pyran-4-yl)-6-(2,2,2-trifluoro-ethoxy)-N-(3-trifluoromethyl-[1,2,4]oxadiazol-5-ylmethyl)-nicotinamide

Participants

Reaction Conditions

Reaction Steps

5-Iodo-6-(2,2,2-trifluoroethoxy)-N-((3-(trifluoromethyl)-1,2,4-oxadiazol-5-yl)methyl)nicotinamide (49.6 mg, 100 μmol), potassium carbonate (39.5 mg, 286 μmol) and PdCl2(dppf) (3.89 mg, 4.76 μmol) were combined to give a light red solid. To this solid was added a solution of 3,6-dihydro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2H-pyran, (CAN 287944-16-5, 0.02 g, 95.2 μmol) in degassed DMF (2 mL). The reaction mixture was stirred at 80° C. overnight, after cooling extracted with i-propyl acetate (2×75 mL) and washed with water (1×10 mL) to pH 7. The organic layers were combined, dried with Na2SO4 and concentrated in vacuo to give a brown oil. The crude material was purified by flash chromatography (silica gel, 10 g, 0% to 10% i-propyl acetate in n-heptane) followed by preparative TLC (silica gel, 1.0 mm, 1:1 n-heptane/i-propyl acetate) to give the title compound (4 mg, 9%) as light brown solid; MS (ESI) 453.1 (M+H)+.

Provenance & Evidence