Bromide ion → {1-[4-(3-Phenyl-7-pyrazol-1-yl-imidazo[1,2-a]pyridin-2-yl)-phenyl]-cyclobutyl}-carbamic acid tert-butyl ester

Participants

Reaction Conditions

Reaction Steps

A mixture of {1-[4-(7-bromo-3-phenyl-imidazo[1,2-a]pyridin-2-yl)-phenyl]-cyclobutyl}-carbamic acid tert-butyl ester (230 mg, 0.44 mmol), pyrazole (39 mg, 0.58 mmol), copper (I) iodide (8.5 mg, 0.044 mmol), potassium phosphate (186 mg, 0.88 mmol) and ethylene diamine (3 μL, 0.044 mmol) in dioxane (2.4 mL) was degassed, placed under an argon atmosphere and heated at 110° C. for 5 hours. On cooling, the reaction was partitioned between aqueous sodium hydrogen carbonate solution and DCM and the organic phase was washed with brine, dried and concentrated in vacuo to give the crude title compound (100 mg). The reaction was repeated using a further 150 mg of the bromide intermediate to give a further batch of the crude title compound (140 mg). Purification by chromotagraphy gave the title compound (200 mg), which was used in the next step without further purification.

Provenance & Evidence