Potassium Iodide → Rac-6-chloro-3-(3-chloro-benzyl)-3-(3,5-dimethoxy-phenyl)-1,3-dihydro-indol-2-one

Participants

Reaction Conditions

Reaction Steps

A mixture of rac-6-chloro-3-(3,5-dimethoxy-phenyl)-1,3-dihydro-indol-2-one (0.1 g, 0.33 mmol) (from Example 40b supra), 3-chlorobenzyl bromide (0.080 g, 0.38 mmol) (Aldrich), potassium iodide (0.065 g, 0.38 mmol) and potassium carbonate (0.098 g, 0.71 mmol) in acetone (5 mL) was heated at 60° C. for 2 hours. After cooling, mixture was partitioned between ethyl acetate and water. The aqueous layer was extracted with ethyl acetate. The combined organic layer was washed with water and brine, dried (Na2SO4), filtered and concentrated. Residue was purified by chromatography to give rac-6-chloro-3-(3-chloro-benzyl)-3-(3,5-dimethoxy-phenyl)-1,3-dihydro-indol-2-one as a white solid. (Yield 0.1 g, 71.4%).

Provenance & Evidence