Potassium Carbonate → Phthalimide

Participants

Reaction Steps

2-{4-[4-(6-methoxy-pyridin-3-yl)-imidazol-1-yl]-butyl}-isoindole-1,3-dione. To a solution of 5-(1H-imidazol-4-yl)-2-methoxy-pyridine (6.7 g, 38.3 mmoles) in DMF (80 ml) was added potassium carbonate (26.5 g, 192 mmoles) and N-(4-bromobutyl)phthalimide (43.0 g, 153 mmoles) at room temperature under dry conditions. The solution was left stirring at room temperature for 36 hours. The reaction was filtered and the solid was washed with ethyl acetate (25 ml). The filtrate was diluted with ethyl acetate and washed with NH4Cl (sat.) (50 ml), H20 (50 ml), NaCl (sat.) (75 ml), dried over sodium sulfate, filtered, and concentrated. The crude product was purified by flash 40 chromatography using an initial solvent gradient of 99% DCM, 1% MeOH, and 0.1% TEA (1 L), then a solvent gradient of 97% DCM, 3% MeOH, and 0.1% TEA (1 L) to yield 2-14-[4-(6-methoxy-pyridin-3-yl)-imidazol-1-yl]-butyl)-isoindole-1,3-dione (10.09 g, 70%). MH+(377).

Provenance & Evidence