Triphenylphosphine → 3-{3-[1-(4-chloro-phenyl)-1-phenyl-meth-(E)-ylidene]-2-oxo-2,3-dihydro-indol-1-ylmethyl}-benzoic acid methyl ester

Participants

Reaction Conditions

Reaction Steps

To a solution of 3-{[phenyl-(3-phenyl-propynoyl)-amino]-methyl}-benzoic acid methyl ester (369.4 mg, 1 mmol) in THF (5 ml) were added palladium(II) acetate (11.2 mg, 0.05 mmol), triphenylphosphine (26.2 mg, 0.1 mmol), 1-chloro-4-iodobenzene (262.3 mg, 1.1 mmol) and cesium fluoride (456 mg, 3 mmol) at room temperature. The solution was stirred for 3 h at 110° C. under an argon atmosphere. After being quenched with water, the mixture was extracted with ethyl acetate, dried over magnesium sulfate and concentrated under reduced pressure. The residue was purified by flash column chromatography on silica gel eluting with (hexane/ethyl acetate=5/1) to give 3-{3-[1-(4-chloro-phenyl)-1-phenyl-meth-(E)-ylidene]-2-oxo-2,3-dihydro-indol-1-ylmethyl}-benzoic acid methyl ester, yield 297 mg (62%); 1H NMR (CDCl3, 300 MHz) δ ppm 8.00 (s, 1H), 7.92 (d, 1H), 7.50 (d, 1H), 7.26-7.43 (m, 10H), 7.08 (dt, 1H), 6.71 (dt, 1H), 6.59 (d, 1H), 6.52 (d, 1H), 4.95 (s, 2H), 3.90 (s, 3H).

Provenance & Evidence