Pyridine → 5-bromo-2-[(3-chloro-4-fluoro-phenylamino)-(4-chloro-phenyl)-methyl]-1-isopropyl-1H-pyrrole-3-carboxylic acid methyl ester

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Reaction Steps

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).

Provenance & Evidence