Ethyl bromoacetate → ethyl [5-[2-[N-tert-butoxycarbonyl-2-(2-ethoxyphenoxy)ethylamino]propyl]-7-cyanoindolin-1-yl]acetate

Participants

Reaction Steps

To a solution of 5-[2-[N-tert-butoxycarbonyl-2-(2-ethoxyphenoxy)ethylamino]propyl]indoline-7-carbonitrile (300 mg) and cis-dicyclohexano-18-crown-6 (24 mg) in dry tetrahydrofuran (4 ml) were added potassium carbonate (107 mg) and ethyl bromoacetate (129 mg), and the mixture was reacted in a sealed tube at 100° C. for 24 hours. To the reaction mixture was added water, and the mixture was extracted with ethyl acetate. The extract was washed with water, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by medium pressure liquid column chromatography on silica gel using a mixture of hexane and ethyl acetate (1/2) as eluent to give 124 mg of ethyl [5-[2-[N-tert-butoxycarbonyl-2-(2-ethoxyphenoxy)ethylamino]propyl]-7-cyanoindolin-1-yl]acetate as an oil.

Provenance & Evidence