Water → 4-oxo-8-phenyl-4,5-dihydro-3H-pyrrolo[2,3-c]quinoline 1-ethyl carboxylate

Participants

Reaction Conditions

Reaction Steps

17 mg (0.025 mmol) of dichlorobis(triphenylphosphine)-palladium (II), 45 mg (0.37 mmol) of phenylboronic acid and 0.6 mL (1.2 ml) of a 2M aqueous solution of potassium carbonate are added to a degassed solution of 100 mg (0.25 mmol) of 8-bromo-4-oxo-4,5-dihydro-3H-pyrrolo[2,3-c]quinoline-1-ethyl carboxylate dissolved in 5 mL of anhydrous dioxan. The reaction mixture is stirred at 110° C. for 20 hours. Water is added and the product is extracted with ethyl acetate. The organic phases are washed with a saturated aqueous solution of sodium chloride, dried over magnesium sulfate, filtered and evaporated. The residue is purified by chromatography on silica (eluent dichloromethane/methanol 98/2) then triturated in methanol to give 16 mg (19%) of 4-oxo-8-phenyl-4,5-dihydro-3H-pyrrolo[2,3-c]quinoline-1-ethyl carboxylate in the form of a white solid.

Provenance & Evidence