Pyridine → (2-{[3-Chloro-4-(2-methylbenzoyl)phenyl]amino}phenyl)-carbamic acid phenethyl ester

Beteiligte Stoffe

Reaktionsschritte

The reactions were conducted under an argon atmosphere. A solution of 2-phenylethanol (0.108 mL) in DCM (2.5 mL, 0.90 mmol) was cooled to 0° C. A mixture of bis(trichloromethyl)carbonate (0.097 g, 0.33 mmol) and pyridine (0.07 mL, 0.90 mmol) in DCM (2.5 mL) was added slowly under stirring. The reaction mixture was stirred for 2 h at room temperature and then filtered, and concentrated in vacuo. The residue was dissolved in DCM (2.5 mL) and {2-chloro-4-[(2-aminophenyl)amino]phenyl}(2-methylphenyl)methanone (0.150 g, 0.45 mmol)(disclosed in WO 98/32730) and potassium carbonate (0.25 g, 1.78 mmol) were added. The reaction mixture was stirred at room temperature for 48 h after which it was poured into a mixture of water and Et2O. The aqueous phase was extracted with more Et2O. The combined organic phases were washed with water, brine, dried (MgSO4), filtered and concentrated in vacuo. The crude product was purified by flash chromatography using EtOAc/petroleum ether 1:3 as the eluent to afford the title compound.

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