Cesium carbonate → Methyl 2-{3-[(tert-butoxycarbonyl)(4-methoxyphenyl)amino]propyl}-1-oxo-1,2-dihydroisoquinoline-7-carboxylate

Participants

Reaction Steps

To a solution of methyl 2-(3-bromopropyl)-1-oxo-1,2-dihydroisoquinoline-7-carboxylate (0.19 g, 0.60 mmol) dissolved in DMF (10 mL) was added tert-butyl (4-methoxyphenyl)carbamate (0.20 g, 0.89 mmol), tetra-n-butylammonium iodide (0.44 g, 1.19 mmol) and cesium carbonate (0.39 g, 1.19 mmol). The reaction mixture was stirred at rt for 6 h. The mixture was diluted with water and extracted with EtOAc (2×). The combined organic phases were then washed with water, and brine, dried over anhydrous Na2SO4, filtered and concentrated. The residue was purified by flash silica gel chromatography (0% to 60% EtOAc/hexanes) to afford methyl 2-{3-[(tert-butoxycarbonyl)(4-methoxyphenyl)amino]propyl}-1-oxo-1,2-dihydroisoquinoline-7-carboxylate (0.11 g, 38%). LC-MS: (FA) ES+ 467.

Provenance & Evidence