Ethyl Acetate → 4-{4-[3-(5,7-Difluoro-quinolin-6-yl methyl)-imidazo[1,2-b]pyridazin-6-yl]-pyrazol-1-yl}-piperidine-1-carboxylic acid tert-butyl ester

Participants

Reaction Conditions

Reaction Steps

6-(6-Chloro-imidazo[1,2-b]pyridazin-3-ylmethyl)-5,7-difluoro-quinoline (Stage 171.2, 264 mg, 0.798 mmol) was dissolved in DME (2.5 mL) in a microwave reactor with 4-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-pyrazol-1-yl]-piperidine-1-carboxylic acid tert-butyl ester (see Stage 180.1, 301 mg, 0.798 mmol), and a solution of 2 M Na2CO3 (1.44 mL). Then tetrakis-(triphenylphosphine)-palladium (46.1 mg, 0.040 mmol) was added and the RM was heated at 150° C. for 5 min under microwave irradiations. It was then taken up with EtOAc and washed with 10% Na2CO3 sol. and brine. The organic layer was dried over Na2SO4 and the solvent was removed. The residue was purified by flash chromatography (CombiFlash® Companion System®, with RediSep® silica gel column, 0 to 20% MeOH in DCM) to afford after evaporation of the solvent the title compound as a pale yellow solid (tR 1.3 min (conditions 2), MH+=546).

Provenance & Evidence