Methyl iodide → 6-Chloro-2-(4-chlorophenyl)-3-((2,5-dimethyl-2H-1,2,3-triazol-4-yl)methyl)imidazo[1,2-a]pyridine

Participants

Reaction Steps

To a suspension of the 6-chloro-2-(4-chlorophenyl)-3-((5-methyl-2H-1,2,3-triazol-4-yl)methyl)imidazo[1,2-a]pyridine (0.6-1.7 mmol, 1.0 eq) in DMF or THF (5-20 mL) was added potassium carbonate (3-5 eq) and either methyliodide or ethyliodide (3-5 eq) and the reaction mixture was heated at 75-85° C. for 18 h. After this time the reaction mixture was cooled and diluted with water (20-50 mL) and ethyl acetate (20-50 mL) and the layers were separated. The aqueous layer was extracted with ethyl acetate (10-30 mL) and the combined organic layers were dried over Na2SO4, concentrated and the residue was purified by chromatography (silica gel, heptane/ethyl acetate gradient) or reverse phase preparatory HPLC (acetonitrile/water gradient) to obtain the desired product. (0.14 g, 26% yield). M/e+ 372.1 for C18H15Cl2N5 (M+H)+; 1H-NMR (500 MHz, CDCl3, δ) 8.09 (d, J=2.0 Hz, 1H), 7.69-7.67 (m, 2H), 7.58 (d, J=9.5 Hz, 1H), 7.45-7.44 (m, 2H), 7.17 (dd, J=9.5, 2.0 Hz, 1H), 4.33 (s, 2H), 4.05 (s, 3H), 2.01 (s, 3H).

Provenance & Evidence