Potassium Carbonate → 5-(2-chloro-phenyl)-1-[4-(1-BOC-1,2,3,6-tetrahydropyridin-4-yl)-phenyl]-3-[di-(trifluoromethyl)-hydroxy-methyl]-4,5-dihydro-1H-pyrazole

Participants

Reaction Conditions

Reaction Steps

1-(4-Bromo-phenyl)-5-(2-chloro-phenyl)-3-[di-(trifluoromethyl)-hydroxy-methyl]-4,5-dihydro-1H-pyrazole (500.0 mg, 1.00 mmol) prepared in Step 5 of Preparation 24, tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-5,6-dihydropyridin-1(2H)-carboxylic acid (370.0 mg, 1.20 mmol), potassium carbonate (690.0 mg, 4.98 mmol), and Pd(dppf)Cl2 (73.0 mg, 0.10 mmol) were added to a mixed solvent of 1,4-dioxane (15.0 mL) and distilled water (4.0 mL). The reaction mixture was stirred at 85° C. for 16 hours. Distilled water was added to the reaction mixture, which was then extracted with ethyl acetate. The extract was washed with distilled water and 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=1/5) to give 435.0 mg of the titled compound as a yellow liquid.

Provenance & Evidence