Potassium Carbonate → HCID 90460873, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of (R/S) ethyl 5-iodo-3-methyl-1-(oxan-2-yl)-1H-pyrazole-4-carboxylate (440 mg, 1.21 mmol, 1.00 equiv), 2-[3-(2-methoxyethoxy)-5-(trifluoromethyl)phenyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (500 mg, 1.44 mmol, 0.97 equiv), Pd(dppf)Cl2 (132 mg, 0.18 mmol, 0.12 equiv) and potassium carbonate (497 mg, 3.60 mmol, 2.40 equiv) in 1,4-dioxane (50 mL) and water (5 mL) was stirred under nitrogen at 100° C. for 3 h. The resulting mixture was cooled to room temperature then diluted with water (30 mL). The resulting solution was extracted with 3×30 mL of ethyl acetate. The combined organic layers were washed with 3×100 mL of brine, dried over anhydrous sodium sulfate and concentrated under vacuum. The residue was purified on a silica gel column eluted with 0-20% of ethyl acetate in petroleum ether to give 410 mg (74%) of (R/S) ethyl 5-(3-(2-methoxyethoxy)-5-(trifluoromethyl)phenyl)-3-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazole-4-carboxylate as a yellow oil. LCMS (method D, ESI): RT=1.70 min, m/z=457.0 [M+H]+.

Provenance & Evidence