6-(4-Trifluoromethylphenyl)-nicotinic acid synthesis

Yield:253315-23-0 30%

Reaction Conditions:

with anhydrous sodium carbonate;tetrakis-(triphenylphosphine)-palladium in tetrahydrofuran at 150; for 0.333333 h;Microwave;

Steps:

17.a

6-Chloronicotinic acid (1.57g, O.Olmmol), [4-(trifluoromethyl) phenyl]boronic acid (1.9g, O.Olmol), tetrakis(triphenylphosphine) palladium (0) (230mg, 2mol%), Na₂CO₃ (2M, 5ml) in THF (15ml) were placed in a microwave tube and the contents were heated in the microwave oven for 20min at 150⁰C. The cooled mixture was filtered through Hyflo to remove inorganic material, the Hyflo was washed with EtOAc and the combined organic extracts were dispersed between aq. NaOH and EtOAc. The aqueous extracts were acidified (aq. HCl) and extracted with EtOAc; the organic extracts were washed with brine, dried (MgSO₄) and evaporated to give the product (0.8g, 30%). ¹H NMR (400 MHz, CD₃OD) δ: 7.85 (2H, d, J 8.2), 8.10 (IH, dd, J 0.8, 8.4), 8.31 (2H, d, J 8.2), 8.49 (IH, dd, J 2.2, 8.2), 9.26 (IH, dd, J 0.8, 2.1).

References:

WO2006/43064,2006,A1 Location in patent:Page/Page column 51