Cesium carbonate → Ethyl 8-[(4-bromo-2-cyanophenyl)amino]-1-methyl-4,5-dihydro-1H-pyrazolo[4,3-h]quinazoline-3-carboxylate

Participants

Reaction Conditions

Reaction Steps

To a solution of ethyl 8-amino-1-methyl-4,5-dihydro-1H-pyrazolo[4,3-h]quinazoline-3-carboxylate (207 mg, 0.753 mmol) in dioxane (6 mL), 5-bromo-2-iodobenzonitrile (260 mg, 0.627 mmol) and cesium carbonate (290 mg, 0.753 mmol) were added and the flask was evacuated and backfilled with argon. [Pd2(dba)3] (13 mg, 0.014 mmol) and X-phos (19 mg, 0.033 mmol) were then charged and the mixture was heated at 80° C. under argon for 8 hours. After cooling to room temperature, the reaction mixture was concentrated, suspended in water (10 mL) and extracted with ethyl acetate. The organic phase was anidrified on Na2SO4, filtered and evaporated to dryness, the crude solid was purified by flash chromatography on silica gel (eluant: dichloromethane/methanol 98/2) to afford 70 mg (20% yield) of the title compound.

Provenance & Evidence