Pyrazole → tert-butyl (1-{4-[3-phenyl-6-(1H-pyrazol-1-yl)imidazo[1,2-a]pyridin-2-yl]phenyl}cyclobutyl)carbamate

Participants

Reaction Conditions

Reaction Steps

A mixture of tert-butyl {1-[4-(6-bromo-3-phenylimidazo[1,2-a]pyridin-2-yl)phenyl]cyclobutyl}carbamate (see Int 4-18, 230 mg, 0.443 mmol), copper(I) iodide (12.6 mg, 0.07 mmol), 1H-pyrazole (36.5 mg, 0.537 mmol), potassium carbonate (36.5 mg, 0.537 mmol) and quinolin-8-ol (9.73 mg, 0.007 mmol) in 0.6 ml DMSO was heated to 150° C. for 7 h under argon atmosphere. The mixture was triturated with 10% ammonium hydroxide solution and charcoal. After filtration through Celite the filter pad was washed with ethyl acetate. The combined solutions were washed with brine and filtered through a silicone filter. The volatile compounds were removed in vacuo. The crude material was purified by reverse phase HPLC chromatography (Chromatorex RP C-18 10_m; 125*30 mm, acetonitrile/water 30/70->acetonitrile/water 100/0) to give 20 mg of the title compound (9 (Y0 overall yield).

Provenance & Evidence