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 (13.6 g, 31.0 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 (1.77 g, 9.30 mmol) and lithium chloride (3.94 g, 93.0 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 h. The solvent was evaporated and the crude reaction mixture was purified by ISCO chromatography (0 to 3% MeOH in DCM). Product was obtained as an orange solid (10.1 g, 66.0%). LCMS: (AA) ES+, 494, 496. 1H NMR (300 MHz, CDCl3) 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