反应详情

温度

100 °C

To a solution of 3-bromo-1-methyl-6-(2-pyridylmethoxy)pyrrolo[2,3-b]pyridine (0.5 g, 1.57 mmol) in 1,4-dioxane (10 mL) is added methyl 3-oxopiperazine-1-carboxylate (0.271 g, 1.88 mmol) and potassium phosphate (0.467 g, 2.20 mmol). The mixture is degassed with nitrogen for 15 minutes, then copper(I) iodide (0.060 g, 0.31 mmol) and N,N′-dimethylethylenediamine (0.055 g, 0.63 mmol) are added. The reaction vessel is sealed and heated at 100° C. for 16 h. The reaction is cooled to room temperature, quenched with water (50 mL) and extracted with EtOAc (3×100 mL). The combined organic layers are dried over anhydrous sodium sulphate, filtered and concentrated in vacuo. The residue is purified by column chromatography on neutral alumina, eluting with 1% MeOH in DCM. The resultant product is triturated with Et2O/pentane (1:1) to afford the title compound (0.5 g, 1.26 mmol) as an off white solid. MS (m/z): 396 (M+1). 1H-NMR (400 MHz, DMSO-d6): δ 3.66 (s, 3H), 3.68 (s, 3H), 3.75 (m, 4H), 4.14 (s, 2H), 5.49 (s, 2H), 6.66 (d, 1H), 7.30-7.33 (m, 2H), 7.50 (d, 1H), 7.77-7.82 (m, 2H), 8.56 (d, 1H).

1. customThe mixture is degassed with nitrogen for 15 minutes
2. customThe reaction vessel is sealed
3. temperatureThe reaction is cooled to room temperature
4. customquenched with water (50 mL)
5. extractionextracted with EtOAc (3×100 mL)
6. dry with materialThe combined organic layers are dried over anhydrous sodium sulphate
7. filtrationfiltered
8. concentrationconcentrated in vacuo
9. customThe residue is purified by column chromatography on neutral alumina
10. washeluting with 1% MeOH in DCM
11. customThe resultant product is triturated with Et2O/pentane (1:1)