反应详情

To a round bottomed flask was added 4-(3-chloropyrazin-2-yloxy)aniline (1.2276 g, 5.54 mmol) dissolved in a mixture of THF (8.86 mL) and NMP (2.215 mL). Iron(iii) acetylacetonate (0.098 g, 0.277 mmol) was added and the temperature was brought to 0° C. (Tetrahydro-2H-pyran-4-yl)magnesium chloride (8.31 mL, 6.65 mmol) was added dropwise to the reaction mixture. Upon completion, the reaction was quenched with saturated ammonia chloride solution. The reaction mixture was diluted with water and extracted with EtOAc. The organic extract was washed with water, brine, dried with magnesium sulfate, filtered, and concentrated. The crude product was adsorbed onto a plug of silica gel and chromatographed through a Redi-Sep® pre-packed silica gel column (120 g), eluting with a gradient of 10% to 100% EtOAc in hexane, to provide 4-(3-(tetrahydro-2H-pyran-4-yl)pyrazin-2-yloxy)aniline.

1. customwas brought to 0° C.
2. additionwas added dropwise to the reaction mixture
3. customUpon completion, the reaction was quenched with saturated ammonia chloride solution
4. additionThe reaction mixture was diluted with water
5. extractionextracted with EtOAc
6. extractionThe organic extract
7. washwas washed with water, brine
8. dry with materialdried with magnesium sulfate
9. filtrationfiltered
10. concentrationconcentrated
11. customchromatographed through a Redi-Sep® pre-packed silica gel column (120 g)
12. washeluting with a gradient of 10% to 100% EtOAc in hexane