Tetrahydrofuran → 5-Cyclohex-1-enyl-6-(2,2,2-trifluoroethoxy)nicotinic acid methylester

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Reaction Conditions

Reaction Steps

5-Bromo-6-(2,2,2-trifluoroethoxy)-3-pyridinecarboxylic acid methyl ester (CAN 1211589-51-3), 200 mg, 637 μmol), 2-cyclohexenyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (CAN 141091-37-4, 119 mg, 123 μA, 574 μmol), K3PO4 (409 mg, 1.91 mmol) and PdCl2(dppf)-CH2Cl2 adduct (26.0 mg, 31.8 μmol) were combined in degassed DMF (4.38 mL)/THF (1.46 mL) to give a yellow suspension. The mixture was heated to 70° C. and shaken overnight. After cooling the mixture was poured into 100 mL saturated NaHCO3/ice water and extracted with i-propyl acetate (2×100 mL). The organic layers were washed with ice/brine (1×150 mL), combined, dried with Na2SO4 and concentrated in vacuo to give 283 mg of a brown oil. The crude material was purified by preparative TLC (silica gel, 2×2.0 mm, n-heptane/iPrOAc 9:1) to give the title compound (129 mg, 64%) as colorless solid; MS (ESI) 316.2 (M+H)+.

Provenance & Evidence