Potassium Phosphate, Tribasic → 5-Cyclohex-1-enyl-N-(pyridin-3-yl)-6-(2,2,2-trifluoroethoxy)nicotinamide

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Reaction Conditions

Reaction Steps

5-Iodo-N-(pyridin-3-yl)-6-(2,2,2-trifluoroethoxy)nicotinamide (0.05 g, 118 μmol), 2-cyclohexenyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (CAN 141091-37-4, 22.1 mg, 22.9 μl, 106 mmol) and potassium phosphate (75.2 mg, 355 μmol) were combined in degassed DMF (1.1 ml)/THF (367 μl) to give a yellow solution which was heated to 80° C. and stirred for 2 days. After cooling the mixture was poured into 5 mL saturated NaHCO3 solution and extracted with i-propyl acetate (2×50 mL). The organic layers were combined, dried with Na2SO4 and concentrated in vacuo to give a brown oil that was purified by preparative TLC (silica gel, 2.0 mm, 1:2 n-heptane/1-propyl acetate) to give the title compound (19 mg, 42%) as light yellow solid; MS (ESI) 378.2 (M+H)+.

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