Lithium Chloride → N-(4-(4-bromo-5-(1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazol-2-yl)thiazol-2-yl)pyridin-2-yl)acetamide

Participants

Reaction Conditions

Reaction Steps

A mixture of 2,4-dibromo-5-(1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazol-2-yl)thiazole (13.62 g, 31.01 mmol), N-[4-(trimethylstannyl)pyridin-2-yl]acetamide (11.1 g, 37.2 mmol), tetrakis(triphenylphosphine)palladium(0) (1.792 g, 1.550 mmol), copper(I) iodide (1.772 g, 9.302 mmol) and lithium chloride (3.944 g, 93.02 mmol) in 1,4-dioxane (569 mL) was degassed with argon. The mixture was sonicated for 20 min and then heated at 120° C. for 5 hrs. Solvent was evaporated and the crude reaction mixture was purified by ISCO chromatography, eluted with MeOH in DCM, 0-3%. Product was obtained as an orange solid (10.13 g, 66.0%). LCMS: (AA) ES+, 494, 496. NMR (300 MHz, d1-chloroform) δ: 8.65 (s, 1H) 8.44 (br, 1H) 8.34 (d, 1H) 7.60 (dd, 1H) 7.30 (d, 2H) 5.30 (s, 2H) 3.40 (t, 2H) 2.25 (s, 3H) 0.86 (t, 2H) −0.05 (s, 9H).

Provenance & Evidence