反应详情

温度

0 °C

To a stirred suspension of sodium hydride (60% in mineral oil, 0.30 g, 7.4 mmol) in DMF (15 mL) under an atmosphere of nitrogen cooled to 0° C. was added methyl 1-oxo-1,2-dihydroisoquinoline-7-carboxylate (1.0 g, 4.9 mmol) in DMF (15 mL) dropwise. The mixture was stirred for 30 mins, then 1,3-dibromopropane (80 μL, 1.28 mmol) was added quickly and the resulting solution was stirred overnight warming to rt slowly. 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 (0% to 30% EtOAc/hexanes) to afford methyl 2-(3-bromopropyl)-1-oxo-1,2-dihydroisoquinoline-7-carboxylate (0.60 g, 38%). LC-MS: (FA) ES+ 326.

1. stirringthe resulting solution was stirred overnight
2. temperaturewarming to rt slowly
3. customThe reaction was quenched with water
4. extractionextracted with EtOAc (2×)
5. washThe combined organic phases were then washed with water, and brine
6. dry with materialdried over anhydrous Na2SO4
7. filtrationfiltered
8. concentrationconcentrated
9. customThe residue was purified by flash silica gel chromatography (0% to 30% EtOAc/hexanes)