4-Bromoanisole → Methyl 2-(4-methoxyphenyl)-1-oxo-1,2-dihydroisoquinoline-7-carboxylate

Participants

Reaction Conditions

Reaction Steps

To a solution of methyl 1-oxo-1,2-dihydroisoquinoline-7-carboxylate (80 mg, 0.4 mmol) and p-bromoanisole (73.9 μL, 0.6 mmol) in dimethyl sulfoxide (2 mL) was added L-proline (18 mg, 0.16 mmol), potassium carbonate (0.11 g, 0.79 mmol) and copper(I) iodide (15 mg, 0.079 mmol). The reaction mixture was heated to 120° C. and stirred overnight. The mixture was then cooled to rt, water added and extracted with DCM (15 mL, 3×). The combined organic phases were then washed with water, and brine, dried over anhydrous Na2SO4, filtered and concentrated. The crude residue was purified by flash silica gel chromatography (0% to 50% EtOAc/hexanes) to afford methyl 2-(4-methoxyphenyl)-1-oxo-1,2-dihydroisoquinoline-7-carboxylate (30 mg, 20%). LC-MS: (FA) ES+ 310.

Provenance & Evidence