Potassium Carbonate → 1-[3-(2-methoxy-phenyl)-1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrrolo[2,3-b]pyridin-5-yl]-piperidine-3-carboxylic acid dimethylamide

Participants

Reaction Steps

To a microwave reaction vial were added 5-bromo-3-(2-methoxy-phenyl)-1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrrolo[2,3-b]pyridine (220 mg, 0.5 mmol), copper (I)-iodide (26 mg, 0.067 mmol), proline (0.13 mmol), potassium cabonate (280 mg, 1.5 mmol) and pyrrolidine-3-carboxylic acid dimethylamide (260 mg, 1.67 mmol). The vial was purged with nitrogen and DMSO (2.0 ml) was added. The mixture was sealed and irradiated in the microwave to 140° C. for 1 hour. The mixture was then partitioned between ethyl acetate (20 ml) and water (20 ml). The layers were separated and the aqueous layer was further extracted with ethyl acetate (10 mL). The combined organic layers were dried over Sodium sulfate, filtered, and concentrated in vacuo. The residue was purified by flash chromatography on silica gel (0% to 100% ethyl acetate in hexanes) to give 151 mg (˜60% with minor impurity) of 1-[3-(2-methoxy-phenyl)-1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrrolo[2,3-b]pyridin-5-yl]-piperidine-3-carboxylic acid dimethylamide as a yellowish oil. MS: m/z 509.3 (M+H+).

Provenance & Evidence