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

Participants

Reaction Conditions

Reaction Steps

A mixture of potassium phosphate tribasic (633 mg, 2.98 mmol), N1,N2-dimethylcyclohexane-1,2-diamine (141 mg, 0.99 mmol), copper(i) iodide (189 mg, 0.99 mmol), 1-(4-bromo-2-methoxyphenoxy)-2-methylpropan-2-ol (328 mg, 1.19 mmol) Part A and commercially available 4-(benzyloxy)pyridin-2(1H)-one (200 mg, 0.99 mmol) in dioxane (1.0 mL) was stirred in a sealed tube at 110° C. for 60 min. After removal of the solids by filtration and concentration of the filtrate, the crude product was subjected to flash chromatography (silica gel/CH2Cl2-10% MeOH/CH2Cl2 100:0 to 0:100 gradient employing LC-MS to identify fractions containing the desired product). The semi-pure product thus obtained was further purified by prep-HPLC (C18 column/Water:MeOH:TFA 90:10:0.1 to 10:90:0.1 gradient) to obtain 4-(benzyloxy)-1-(4-(2-hydroxy-2-methylpropoxy)-3-methoxyphenyl)pyridin-2(1H)-one D-1 (298 mg, 74.3% yield) as a white foam. LC/MS 396 (M+H)+, tR 0.87 min (method 5); 1H NMR (400 MHz, Chloroform-D) δ ppm 7.34-7.47 (5H, m), 718 (1H, d, J=7.78 Hz), 6.96 (1H, d, J=8.53 Hz), 6.80-6.90 (2H, m), 6.28 (1H, d, J=2.51 Hz), 6.16 (1H, dd, J=7.65, 2.64 Hz), 5.08 (2H, s), 3.85 (5H, s), 1.35 (6H, s).

Provenance & Evidence