反应详情

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).

1. temperatureheated
2. temperatureto reflux overnight
3. temperatureThe reaction is cooled
4. additionpoured onto brine (ca. 500 mL)
5. extractionthe product extracted with CHCl3 (ca. 2×300 mL)
6. dry with materialThe combined organic extracts are dried over magnesium sulphate
7. filtrationfiltered
8. concentrationconcentrated in vacuo
9. customto give a yellow oil
10. customThis is purified by column chromatography on silica
11. washeluting with 0 to 90% EtOAc in hexane