Potassium Fluoride → 4-methyl-3-[4-(3-methyl-3H-imidazol-4-yl)-pyrazol-1-yl]-benzoic acid ethyl ester

Participants

Reaction Conditions

Reaction Steps

3-(4-Bromo-pyrazol-1-yl)-4-methyl-benzoic acid ethyl ester (Example 8) (366 mg, 1.18 mmol) was dissolved in dioxane (2 mL) and flushed with nitrogen. 1-Methyl-5-tributylstannanyl-1H-imidazole (366 mg, 0.986 mmol) was added to the reaction flask in dioxane (0.5 mL) then the flask was purged with N2. After Pd(PPh3)4 (85 mg, 0.074 mmol) was added, the reaction was heated to 100° C. in a sealed tube. The reaction mixture was stirred with a 10% KF solution for 30 min then diluted with EtOAc. The layers were separated and the aqueous layer extracted with EtOAc (3×). The organic layers were combined, dried over Na2SO4, and concentrated. The resulting residue was purified by chromatography on silica gel (5% MeOH/CH2Cl2) to give the title compound (81 mg, 22%) as a colorless oil.

Provenance & Evidence