Potassium Phosphate, Tribasic → 1-(4-(2-hydroxy-2-methylpropoxy)-3-methoxyphenyl)-4-(4-(1,1,2,2-tetrafluoroethoxy)phenyl)pyridin-2(1H)-one

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A mixture of 1-(4-(2-hydroxy-2-methylpropoxy)-3-methoxyphenyl)-2-oxo-1,2-dihydropyridin-4-ylboronic acid Part A (20 mg, 0.06 mmol), 1-bromo-4-(1,1,2,2-tetrafluoroethoxy)benzene (24.6 mg, 0.09 mmol), potassium phosphate, tribasic (32 mg, 0.15 mmol), and PalladiumTetrakis (4 mg, 3.00 μmol) in DMF (0.6 mL) was stirred under nitrogen at 80° C. overnight. The mixture was filtered, concentrated, and was purified using HPLC (Phen Luna Axia C18 5μ 10:90:0.1 to 90:10:0.1 MeOH—H2O-TFA). The product was repurified using ISCO flash chromatography (silica gel/hexanes/ethyl acetate/methanol 100:0 to 0:90:10 gradient) to afford the desired product 1-(4-(2-hydroxy-2-methylpropoxy)-3-methoxyphenyl)-4-(4-(1,1,2,2-tetrafluoroethoxy)phenyl)pyridin-2(1H)-one B-6 (16.43 mg, 0.032 mmol, 54.0% yield) as a light yellow solid. LC/MS 482 (M+H)+, tR 0.92 min (method 5). 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 7.63-7.67 (2H, m), 7.43 (1H, d, J=7.26 Hz), 7.34 (2H, d, J=8.58 Hz), 6.97-7.03 (2H, m), 6.90-6.96 (1H, m), 6.87 (1H, d, J=1.76 Hz), 6.49 (1H, dd, J=7.26, 1.98 Hz), 5.80-6.11 (1H, m), 3.89 (3H, s), 3.88 (2H, s), 1.37 (6H, s)

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