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

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Reaction Conditions

Reaction Steps

In a sealed tube, 30 mg (0.14 mmol) of 3-bromomethylphenylboronic acid is dissolved in 100 μL of a 40% aqueous solution of dimethylamine and the solution is heated at 100° C. for 4 hours. The solvents are evaporated and the residue is taken up in 1.5 mL of anhydrous dioxan. The solution is degassed before adding 38 mg (0.14 mmol) of 8-bromo-4-oxo-4,5-dihydro-3H-pyrrolo[2,3-c]quinoline-1-ethyl carboxylate, 13 mg (0.028 mmol) of dichlorobis(triphenylphosphine)-palladium (11) and 200 μL (0.4 mmol) of a 2M aqueous solution of tribasic potassium triphosphate. The reaction mixture is stirred at II 0° 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 chloroform/methanol/ammonia 90/25/4) to give 5 mg (10%) of 8-(3-dimethylaminomethyl-phenyl)-4-oxo-4,5-dihydro-3H-pyrrolo[2,3-c]quinoline-1-ethyl carboxylate in the form of a beige solid.

Provenance & Evidence