Potassium Carbonate → 1-(2-chloro-phenyl)-5-[3-(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

5-(3-Bromo-phenyl)-1-(2-chloro-phenyl)-3-[di-(trifluoromethyl)-hydroxy-methyl]-4,5-dihydro-1H-pyrazole (1.1 g, 2.2 mmol) prepared in Step 4 of Preparation 16, tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-5,6-dihydropyridin-1 (2H)-carboxylic acid (805.5 mg, 2.6 mmol), potassium carbonate (900.0 mg, 6.5 mmol), and Pd(dppf)Cl2 (159.0 mg, 0.20 mmol) were added to a mixed solvent of 1,4-dioxane (35.0 mL) and distilled water (9.0 mL). The reaction mixture was stirred for 15 minutes, additionally at 90° C. for 16 hours, and then ethyl acetate was added thereto. The reaction mixture 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=1/4) to give 820.0 mg of the titled compound as a white solid.

Provenance & Evidence