Potassium Phosphate, Tribasic → 4-chloro-1-(3-methoxy-4-((2-(trimethylsilyl)ethoxy)methoxy)phenyl)pyridin-2(1H)-one

Participants

Reaction Conditions

Reaction Steps

N1,N2-dimethylcyclohexane-1,2-diamine (140 μL, 0.81 mmol) was added to a mixture of commercially available 4-chloropyridin-2(1H)-one (150 mg, 1.16 mmol), (2-((4-bromo-2-methoxyphenoxy)methoxy)ethyl)trimethylsilane (463 mg, 1.39 mmol), preparation described in Part G of Procedure 1, K3PO4 (737 mg, 3.47 mmol), and Copper (I) Iodide (154 mg, 0.81 mmol) in Dioxane (6 mL). The mixture was stirred at 100° C. overnight. The reaction was diluted with DCM, washed with sat. NaHCO3, dried (Na2SO4), and concentrated. The crude was subjected to ISCO flash chromatography (silica gel/hexanes/ethyl acetate 100:0 to 0:100 gradient) to afford the desired product 4-chloro-1-(3-methoxy-4-((2-(trimethylsilyl)ethoxy)methoxy)phenyl)pyridin-2(1H)-one 14A (358 mg, 0.94 mmol, 81% yield) as a light yellow solid. LC/MS 382 (M+H)+, tR 1.06 min (method 5).

Provenance & Evidence