2-Methyl-3-butyn-2-ol → 8-(3-hydroxy-3-methyl-but-1-ynyl)-4-oxo-4,5-dihydro-3H-pyrrolo[2,3-c]quinoline 1-ethyl carboxylate

Participants

Reaction Conditions

Reaction Steps

50 mg (0.26 mmol) of copper iodide, 69 mg (0.68 mmol) of triethylamine and 37 mg (0.05 mmol) of dichlorobis(triphenylphosphine)-palladium (II) are added to a suspension of 200 mg (0.52 mmol) of 8-iodo-4-oxo-4,5-dihydro-3H-pyrrolo[2,3-c]quinoline-1-ethyl carboxylate in 5 ml of anhydrous dioxan, then this mixture is degassed under argon. After 15 minutes, 66 mg (0.78 mmol) of 2-methyl-but-3-yn-2-ol are added, then the mixture is heated at 100° C. for 1 hour. The raw reaction product is then filtered on celite, the filtrate is evaporated to dryness and the residue is purified by chromatography on silica (ethyl acetate), then the product is triturated in methanol to give 135 mg (76%) of 8-(3-hydroxy-3-methyl-but-1-ynyl)-4-oxo-4,5-dihydro-3H-pyrrolo[2,3-c]quinoline-1-ethyl carboxylate in the form of a white solid.

Provenance & Evidence