反应详情

Pyridine (5.59 mmol), DMAP (0.486 mmol) and then Ms2O (4.22 mmol) were added to a solution of 5-bromo-2-[(4-chloro-phenyl)-hydroxy-methyl]-1-isopropyl-1H-pyrrole-3-carboxylic acid methyl ester (step D3) (1.622 mmol) in CH2Cl2 (20 mL) and the reaction mixture was stirred at rt 17.5 h. The reaction mixture was diluted with H2O/brine and extracted with CH2Cl2 (3×). The combined organic layers were dried (Na2SO4), filtered and concentrated. The residue was diluted with CH2Cl2 (20 mL) and 3-chloro-4-fluoroaniline [367-21-5] (1.865 mmol) was added and the mixture was stirred at rt for 20.5 h. The reaction mixture was diluted with H2O/brine and extracted with CH2Cl2 (3×). The combined organic layers were washed with brine, dried (Na2SO4), filtered and concentrated. The residue was purified using a RediSep® silica gel column to afford the title compound as a yellow foam. tR: 6.29 min (HPLC 1); ESI-MS: tR=1.57 min, [M+H]+ 513/515/517 (LC-MS 1); TLC: Rf=0.45 (1:6 EtOAc/heptanes).

1. extractionextracted with CH2Cl2 (3×)
2. dry with materialThe combined organic layers were dried (Na2SO4)
3. filtrationfiltered
4. concentrationconcentrated
5. additionwas added
6. stirringthe mixture was stirred at rt for 20.5 h
7. extractionextracted with CH2Cl2 (3×)
8. washThe combined organic layers were washed with brine
9. dry with materialdried (Na2SO4)
10. filtrationfiltered
11. concentrationconcentrated
12. customThe residue was purified