反应详情

温度

180 °C

Copper (I) iodide (0.98 g, 5.1 mmol) was added to a suspension of 3-(cyclohexyloxy)-2(1H)-pyrazinone (1.0 g, 5.1 mmol, prepared according to the method described in the Journal of Medicinal Chemistry, 52(7), 2076-2089; 2009), 1-bromo-4-fluorobenzene (0.85 mL, 7.7 mmol), N,N′-dimethylethylenediamine (0.55 mL, 5.1 mmol) and K3PO4 (2.18 g, 10.3 mmol) in a mixture of DMF (2 mL) and 1,4-dioxane (8 mL). The reaction mixture was stirred at 180° C. for 15 minutes under microwave irradiation. The solid was filtered off and washed with DCM, the filtrate was treated with a 32% solution of NH4OH. The organic layer was separated, dried (Na2SO4), filtered and the solvent evaporated in vacuo. The crude product was purified by flash column chromatography (silica; AcOEt in DCM 1/99 to 20/80). The desired fractions were collected and the solvents evaporated in vacuo to yield 3-cyclohexyloxy-1-(4-fluoro-phenyl)-1H-pyrazin-2-one (1.13 g, 76% yield).

1. customprepared
2. filtrationThe solid was filtered off
3. washwashed with DCM
4. additionthe filtrate was treated with a 32% solution of NH4OH
5. customThe organic layer was separated
6. dry with materialdried (Na2SO4)
7. filtrationfiltered
8. customthe solvent evaporated in vacuo
9. customThe crude product was purified by flash column chromatography (silica; AcOEt in DCM 1/99 to 20/80)
10. customThe desired fractions were collected
11. customthe solvents evaporated in vacuo