Potassium Carbonate → HCID 66652863, compound

Participants

Reaction Conditions

Reaction Steps

To a mixture of (5-fluoro-2-hydroxyphenyl)boronic acid (225 mg, 1.44 mmol) and 4-bromo-3-nitro-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazole or 4-bromo-5-nitro-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazole (Preparation 22, 498 mg, 1.80 mmol) in 1,2-dimethoxyethane (4.5 mL) and 2 M solution of potassium carbonate in water (2.0 mL) was added tetrakis(triphenylphosphine)palladium(0) (86.71 mg, 0.08 mmol). The mixture was sparged with argon (×3) and heated at 80° C. for 4 hours. Additional 5-fluoro-2-hydroxyphenyl)boronic acid (56 mg) was added and the reaction mixture stirred with heating for 18 additional hours. The reaction mixture was cooled to ambient temperature, diluted with ethyl acetate, and filtered through diatomaceous earth. The layers were separated and the organic layer washed with water and brine, dried over anhydrous magnesium sulfate, filtered, then concentrated in vacuo. The residue was purified by automated silica gel flash chromatography (100% hexanes to 50% ethyl acetate in hexanes gradient elution) to afford the title compound as a light yellow solid (275 mg, 62%).

Provenance & Evidence