1-(2-Diethylaminoethyl)-4-trifluoromethyl-6-iodoisatin → 1-(2-Diethylaminoethyl)-4-trifluoromethyl-6-iodo-3-hydroxy-3-(2-chlorophenyl)oxindole

Participants

Reaction Steps

To a solution of 1-(2-diethylaminoethyl)-4-trifluoromethyl-6-iodoisatin (4 g, 9.09 mmol) in a mixture of diethyl ether (60 mL) and toluene (20 mL) was added dropwise a freshly prepared 0.67 N 2-chlorophenylmagnesium iodide in ether (15 mL, 10.1 mmol) over 20 min at room temperature. The mixture was stirred for 20 min at the same temperature and the reaction was quenched with aqueous NaHCO3. The mixture was extracted with ethyl acetate and the extracts were washed with sat. aqueous NaHCO3, dried over MgSO4, and concentrated. The residue was purified by silica gel column chromatography with 100:1 to 50:1 chloroform/methanol to give the title compound (2.81 g, 56%).

Provenance & Evidence