N,N'-Dimethylethylenediamine → tert-butyl 4-(1-ethyl-6-fluoro-1H-pyrrolo[2,3-b]pyridin-3-yl)-3-oxopiperazine-1-carboxylate

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Reaction Steps

3-Bromo-1-ethyl-6-fluoro-1H-pyrrolo[2,3-b]pyridine (13.00 g, 53.48 mmol), tert-butyl 3-oxopiperazine-1-carboxylate (11.78 g, 58.83 mmol), N,N′-dimethylethane-1,2-diamine (2.36 mL, 21.93 mmol), copper(I) iodide (2.24 g, 11.77 mmol), potassium phosphate (tribasic, n-hydrate) (12.49 g, 58.83 mmol), and 1,4-dioxane (250 mL) are combined under a nitrogen atmosphere with stirring and heated to reflux overnight. The reaction is cooled, poured onto brine (ca. 500 mL) and the product extracted with CHCl3 (ca. 2×300 mL). The combined organic extracts are dried over magnesium sulphate, filtered, and concentrated in vacuo to give a yellow oil. This is purified by column chromatography on silica, eluting with 0 to 90% EtOAc in hexane, to give the title compound as an orange oil (20.039 g, 55.29 mmol). MS (m/z): 363 (M+1).

Provenance & Evidence