Dimethylformamide → 1-(2-Diethylaminoethyl)-4-trifluoromethyl-6-cyano-3-hydroxy-3-(2-naphthyl)oxindole

Participants

Reaction Conditions

Reaction Steps

A mixture of 1-(2-diethylaminoethyl)-4-trifluoromethyl-6-iodo-3-hydroxy-3-(2-naphthyl)oxindole of Example 48 (582 mg, 1, 24 mmol), 60% Zn(CN)2 (172 mg, 0.879 mmol), and (PPh3)4Pd (177 mg, 0.153 mmol) in DMF (6 mL) was stirred for 2.5 h at 80° C. Sat. aqueous NaHCO3 was added. The mixture was extracted with toluene-ethyl acetate, and the extracts were washed with sat. aq. NaHCO3, dried over MgSO4, and concentrated. The residue was purified by silica gel column chromatography with 80:1 to 50:1 chloroform/methanol to give the title compound (382 mg, 66%).

Provenance & Evidence