Oxalyl chloride → 3-Benzo[1,3]dioxol-5-yl-2-[5-(3-trifluoromethyl-phenyl)-furan-2-carbonyl]-1,2,3,4-tetrahydro-pyrrolo[3,4-b]quinolin-9-one

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Reaction Steps

To a solution of 5-(3-trifluoromethylphenyl)-2-furoic acid (80.44 mg, 0.314 mmol) in 1:1 DCM:THF (5 mL, anhydrous) was added oxalyl chloride (43.85 mg, 0.345 mmol), followed by two drops of DMF. The mixture was stirred at room temperature for 1 h. A suspension of 1,2,3,4-tetrahydro-3-(3,4-methylenedioxyphenyl)-9H-pyrrolo-[3,4-b]quinolin-9-one (96.2 mg, 0.314 mmol) (prepared as in Example 5), triethylamine (0.13 mL), and DMAP (trace) in 1:1 DCM:THF (5 mL) was added. The resulting mixture was stirred at room temperature for 16 h. Ethyl acetate (50 mL) was added, and the solution was washed with aq. NaHCO3, brine, 1N HCl, brine and then dried with MgSO4. The solvent was evaporated and the residue triturated with ethyl acetate to yield the product as a white solid.

Provenance & Evidence