Toluene → 2-(4-tert-butoxycarbonylbenzyl)-6-methyl-1-oxo-4-phenyl-1,2-dihydroisoquinoline-3-carboxylic Acid Methyl Ester

Participants

Reaction Conditions

Reaction Steps

A mixture of 6-bromo-2-(4-tert-butoxycarbonylbenzyl)-1-oxo-4-phenyl-1,2-dihydroisoquinoline-3-carboxylic acid methyl ester (500 mg), methylboronic acid (270 mg), tetrakis(triphenylphosphine)palladium(0) (110 mg), potassium carbonate (380 mg), toluene (6 ml) and THF (4 ml) was stirred at 100° C. for 6 hrs. under a nitrogen atmosphere. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with water and saturated brine. The solvent was dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane-hexane:ethyl acetate=2:1) and recrystallized (ethyl acetate-hexane) to give the title compound (380 mg).

Provenance & Evidence