Potassium Carbonate → HCID 86682416, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 5-bromo-8-[(1S,2S)-2-{[tert-butyl(dimethyl)silyl]oxy}cyclohexyl]-8,9-dihydro-7H-pyrrolo[3,4-h]quinolin-7-one (see Example 18, 2.00 g, 4.21 mmol) in a mixture of 20 mL of THF and 2 mL of water under an atmosphere of nitrogen was added potassium vinyltrifluoroborate (0.789 g, 5.89 mmol), potassium carbonate (1.45 g, 10.5 mmol), and bis(tri-tert-butylphosphine)palladium(0) (0.215 g, 0.421 mmol). The mixture was heated at 50° C. for 2 hr, cooled to ambient temperature, poured into saturated aqueous sodium bicarbonate and extracted 2× with ethyl acetate. The combined organic extracts were dried with sodium sulfate, filtered, and concentrated in vacuo. The residue was purified via silica gel chromatography, eluting with 0-60% ethyl acetate in hexanes to provide 8-[(1S,2S)-2{[tert-butyl(dimethyl)silyl]oxy}cyclohexyl]-5-ethenyl-8,9-dihydro-7H-pyrrolo[3,4-h]quinolin-7-one that gave a proton NMR spectra consistent with theory and a mass ion (ES+) of 424.4.

Provenance & Evidence