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

Participants

Reaction Conditions

Reaction Steps

68 mg (0.01 mmol) of dichlorobis(triphenylphosphine)-palladium (II), 92 mg (0.59 mmol) of 2-chlorophenylboronic acid and 1 mL (2 mmol) of a 2M aqueous solution of tribasic potassium triphosphate are added to a degassed solution of 200 mg (0.49 mmol) of 8-bromo-4-oxo-4,5-dihydro-3H-pyrrolo[2,3-c]quinoline-1-ethyl carboxylate dissolved in 10 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) to give 27 mg (15%) of 8-(2-chlorophenyl)-4-oxo-4,5-dihydro-3H-pyrrolo[2,3-c]quinoline-1-ethyl carboxylate in the form of a white solid.

Provenance & Evidence