1-Bromonaphthalene → 8-naphthalen-1-yl-4-oxo-4,5-dihydro-3H-pyrrolo[2,3-c]quinoline 1-ethyl carboxylate

Participants

Reaction Conditions

Reaction Steps

68 mg (0.1 mmol) of dichlorobis(triphenylphosphine)-palladium (11), 149 mg (0.59 mmol) of bis(pinacolo)diborane and 273 μL (1.96 mmol) of triethylamine 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 4 mL of anhydrous dioxan. The reaction mixture is stirred at 110° C. for 4 days. 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 taken up in 5 mL of anhydrous dioxan. The solution is degassed with a stream of nitrogen before adding 81 μL (0.59 mmol) of 1-bromonaphthalene, 69 mg (0.1 mmol) of dichlorobis(triphenylphosphine)-palladium (II) and 1 mL (2 mmol) of a 2M aqueous solution of tribasic potassium triphosphate. 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 (3% in two stages) of 8-naphthalen-1-yl-4-oxo-4,5-dihydro-3H-pyrrolo[2,3-c]quinoline-1-ethyl carboxylate in the form of a beige solid.

Provenance & Evidence