Potassium Iodide → 2-[6-chloro-1-(2-dimethylamino-ethyl)-4-fluoro-1H-indazol-3-yl]-5-(2-trimethylsilanylethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carbaldehyde

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Reaction Steps

2-(6-Chloro-4-fluoro-1H-indazol-3-yl)-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carbaldehyde (100 mg, 0.22 mmol) was dissolved in DMF (0.5 ml) and cooled in an ice bath. Sodium hydride (60% dispersion, 22 mg, 0.56 mmol) was carefully added. The mixture was stirred for 10 min then dimethylaminoethyl chloride hydrochloride (36 mg, 0.25 mmol) and potassium iodide (4 mg, 0.022 mmol) were added and the reaction was warmed to room temperature then stirred at 50° C. overnight. After cooling to room temperature, water and ethyl acetate were added to the reaction. The layers were separated and the aqueous layer was extracted twice more with ethyl acetate. The combined organic layers were washed water and sodium chloride solution and dried over sodium sulfate. After evaporation, the residue was purified by silica gel chromatography (methanol/dichloromethane) to give 46 mg (40%) of 2-[6-chloro-1-(2-dimethylamino-ethyl)-4-fluoro-1H-indazol-3-yl]-5-(2-trimethylsilanylethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carbaldehyde. (M+H)+=517.

Provenance & Evidence