Potassium Carbonate → HCID 118431798, compound

Participants

Reaction Conditions

Reaction Steps

5-(3-Bromo-phenyl)-1-(2-chloro-phenyl)-3-pentafluoroethyl-4,5-dihydro-1H-pyrazole (1.0 g, 2.2 mmol) prepared in Step 1 of Preparation 6, 4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-3,6-dihydro-2H-pyridin-1-carboxylic acid tert-butyl ester (820.0 mg, 2.6 mmol), Pd(dppf)Cl2 (181.0 mg, cat.) and potassium carbonate (915.0 mg, 6.6 mmol) were added to a mixed solvent of 1,4-dioxane (32.0 mL) and distilled water (8.0 mL). The reaction mixture was stirred at 90° C. for 12 hours and then filtered through celite pad. A saturated solution of ammonium chloride was added to the filtrate, which was then extracted with ethyl acetate three times. The combined extract washed with brine, dried on anhydrous magnesium sulfate, and then concentrated under reduced pressure to give a yellow liquid residue. The resulting residue was purified by silica gel column chromatography (eluent: ethyl acetate/n-hexane=1/8) to give 1.1 g of the titled compound as a yellow liquid.

Provenance & Evidence