Toluene → HCID 22176104, compound

Participants

Reaction Steps

A mixture of methyl 6-(benzyloxy)-2-isobutyl-1-oxo-4-trifluoromethanesulfonyloxy-1,2-dihydro-3-isoquinolinecarboxylate (10.26 g, 20 mmol), 2-thiopheneboronic acid (3.07 g, 24 mmol), sodium carbonate (5.30 g, 50 mmol), toluene (50 ml), methanol (10 ml) and water (10 ml) was stirred at room temperature for 30 min under an argon atmosphere. To the resulting mixture was added tetrakis(triphenylphosphine)palladium (1.16 g, 1 mmol), the mixture was refluxed under heating for 10 h under an argon atmosphere. 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 methyl 6-(benzyloxy)-2-isobutyl-1-oxo-4-(2-thienyl)-1,2-dihydro-3-isoquinolinecarboxylate (2.11 g, 23.6%) as crystals.

Provenance & Evidence