Toluene → HCID 22176020, compound

Participants

Reaction Steps

A mixture of tert-butyl(6-bromo-4-butoxy-2-isobutyl-1-oxo-1,2-dihydro-3-isoquinolinyl)methylcarbamate (0.48 g, 1 mmol), phenylboric acid (0.15 g, 1.2 mmol), sodium carbonate (0.26 g, 2.5 mmol), toluene (10 ml), ethanol (2 ml) and water (2 ml) was stirred at room temperature under an argon atmosphere for 30 min. To the resulting mixture was added tetrakis(triphenylphosphine)palladium (58 mg, 0.05 mmol), and then the mixture was refluxed under an argon atmosphere for 10 h. The reaction mixture was poured into water and extracted with ethyl acetate. The extract was washed with brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography to give tert-butyl(4-butoxy-2-isobutyl-1-oxo-6-phenyl-1,2-dihydro-3-isoquinolinyl)methylcarbamate (0.42 g, 89.4%) as crystals.

Provenance & Evidence