Tetrabutylammonium Fluoride → 8-ethynyl-4-oxo-4,5-dihydro-3H-pyrrolo[2,3-c]quinoline 1-ethyl carboxylate

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Reaction Steps

1.2 ml (1.2 mmol) of a 1M solution of tetrabutylammonium fluoride in tetrahydrofuran is added to a solution of 398 mg (1.13 mmol) of 4-oxo-8-trimethylsilanylethynyl-4,5-dihydro-3H-pyrrolo[2,3-c]quinoline-1-ethyl carboxylate in 10 ml of tetrahydrofuran, then the mixture is stirred for 1 hour at room temperature. The solvent is evaporated and the product is extracted with ethyl acetate. The organic phase is washed with a 1M aqueous solution of hydrochloric acid, a saturated solution of sodium chloride, dried over magnesium sulfate, filtered and evaporated. The product is crystallized in a methanol/acetone mixture (4/1) to give 160 mg (50%) of 8-ethynyl-4-oxo-4,5-dihydro-3H-pyrrolo[2,3-c]quinoline-1-ethyl carboxylate in the form of a white solid.

Provenance & Evidence