Sodium hydride → HCID 67282042, compound

Participants

Reaction Steps

To a stirred suspension of sodium hydride (60% in mineral oil, 0.30 g, 7.4 mmol) in DMF (10 mL) under an atmosphere of nitrogen was added methyl 1-oxo-1,2-dihydroisoquinoline-7-carboxylate (1.0 g, 4.9 mmol) in DMF (10 mL) dropwise. The mixture was stirred for 30 mins, then tert-butyl (3-bromopropyl)carbamate (1.76 g, 7.4 mmol) dissolved in DMF (5 mL) was added dropwise via cannula and the resulting solution was stirred at rt overnight. The reaction was quenched 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 (20% to 90% EtOAc/hexanes) to afford methyl 2-{3-[(tert-butoxycarbonyl)amino]propyl}-1-oxo-1,2-dihydroisoquinoline-7-carboxylate (0.99 g, 56%). LC-MS: (FA) ES+ 361.

Provenance & Evidence