Potassium Carbonate → Methyl 2-(1,3-dioxo-5-(pyridin-3-ylmethoxy)isoindolin-2-yl)acetate

Participants

Reaction Conditions

Reaction Steps

To a solution of methyl 2-(5-hydroxy-1,3-dioxoisoindolin-2-yl)acetate (78 mg, 0.332 mmol) in CH3CN (20 mL), K2CO3 (115 mg, 0.829 mmol) and 3-(bromomethyl)-pyridine hydrobromide (126 mg, 0.497 mmol) were added at room temperature. The reaction was heated at 80° C. for 2 hours. The insoluble was filtered off and washed with DCM; the filtrated was evaporated under vacuum; and the crude was partitioned between a saturated solution of Na2CO3 and DCM. The organic phase was washed with brine, dried over sodium sulfate, filtered and evaporated to dryness. The crude was purified by filtration on silica gel cartridge (petroleum ether/EtOAc 1/1 to petroleum ether/EtOAc 2/8) to afford methyl 2-(1,3-dioxo-5-(pyridin-3-ylmethoxy)isoindolin-2-yl)acetate (60 mg, 0.184 mmol, 55.4% yield, MS/ESI+ 327.0 [MH]+).

Provenance & Evidence