反应详情

温度

0 °C

DIPEA (1.18 mL, 6.77 mmol) was added to a solution of rac-1-(3-bromo-phenyl)-1-(1H-pyrazol-3-yl)-ethylamine (1.2 g, 4.51 mmol) in DCM (20 mL) and the mixture was cooled in an ice bath. Then chloroacetyl chloride (0.40 mL, 4.96 mmol) was added and the mixture was stirred at 0° C. for 3 hours. The mixture was diluted with NH4Cl (aq. sat. solution) and extracted with DCM. The organic layer was separated, dried (MgSO4), filtered and the solvents evaporated in vacuo. The crude product was purified by flash column chromatography (silica gel; AcOEt in DCM 0/100 to 20/80). The desired fractions were collected and concentrated in vacuo. The residue was dissolved in EtOH (10 mL) and NaHCO3 (aq. sat. solution) (1 mL) and the mixture was stirred at room temperature for 30 minutes. The mixture was diluted with water and the product extracted with DCM. The combined organic layers were concentrated in vacuo to yield rac-N-[1-(3-bromo-phenyl)-1-(1H-pyrazol-3-yl)-ethyl]-2-chloro-acetamide (1.22 g, 79% yield) as a colourless oil, which was used in the next step without further purification.

1. temperaturethe mixture was cooled in an ice bath
2. extractionextracted with DCM
3. customThe organic layer was separated
4. dry with materialdried (MgSO4)
5. filtrationfiltered
6. customthe solvents evaporated in vacuo
7. customThe crude product was purified by flash column chromatography (silica gel; AcOEt in DCM 0/100 to 20/80)
8. customThe desired fractions were collected
9. concentrationconcentrated in vacuo
10. dissolutionThe residue was dissolved in EtOH (10 mL)
11. stirringNaHCO3 (aq. sat. solution) (1 mL) and the mixture was stirred at room temperature for 30 minutes
12. additionThe mixture was diluted with water
13. extractionthe product extracted with DCM
14. concentrationThe combined organic layers were concentrated in vacuo