Potassium Iodide → 4-{2-[(4-Fluoro-3-trifluoromethyl-benzyl)-methyl-amino]-quinoxalin-6-yl}-pyrazole-1-carboxylic acid tert-butyl ester

Participants

Reaction Conditions

Reaction Steps

A mixture of (6-Bromo-quinoxalin-2-yl)-(4-fluoro-3-trifluoromethyl-benzyl)-methyl-amine (0.35 g, 1 eq, 0.84 mmol), 1-Boc-4-pyrazole boronic acid pinacol ester (0.3 g, 1.2 eq, 1.01 mmol), caesium carbonate (1.1 g, 4.0 eq, 3.3 mmol) and potassium iodide (0.014 g, 0.1 eq, 0.84 mmol) in 1,4-dioxane (15 mL) was degassed at RT under vacuum and then placed under an atmosphere of nitrogen. The process was repeated twice and Fu's catalyst (Bis(tri-tert-butylphosphine)palladium(0)) (0.02 g, 0.05 eq, 0.04 mmol) was added at room temperature. The reaction mixture was heated at 108° C. in a microwave reactor for 180 min. After completion of the reaction (confirmed by TLC), the organic mixture was diluted with ethyl acetate (325 mL) and washed with water (100 mL×3) followed by brine (100 mL). The organic solvent was dried and concentrated to give a solid residue.

Provenance & Evidence