Cesium carbonate → 5-{2-[4-(4-Methyl-piperazin-1-yl)-2-trifluoromethoxy-phenylamino]-pyrimidin-4-yl}-1H-pyrrole-3-carboxylic acid ethyl ester

Participants

Reaction Conditions

Reaction Steps

To a solution of 5-(2-amino-pyrimidin-4-yl)-1H-pyrrole-3-carboxylic acid ethyl ester (400 mg, 1.72 mmol) in dioxane (40 mL), 1-(4-iodo-3-trifluoromethoxy-phenyl)-4-methyl-piperazine (732 mg, 1.90 mmol) and cesium carbonate (1.1 g, 3.45 mmol) were added and the flask was evacuated and backfilled with argon. [Pd2(dba)3] (158 mg, 0.17 mmol) and Xantphos (299 mg, 0.52 mmol) were then charged and the mixture was heated at 80° C. under argon for 16 hours. After cooling to room temperature, the reaction mixture was concentrated, suspended in water (50 mL) and extracted with ethyl acetate. The organic phase was acidified on Na2SO4, filtered and evaporated to dryness, the crude solid was purified by flash chromatography on silica gel (eluant: dichloromethane/methanol 95/5) to afford 126 mg (15% yield) of the title compound.

Provenance & Evidence