5-Chloro-1H-indole-2-carboxylic acid → HCID 86605145, compound

Participants

Reaction Steps

To a stirring suspension of 1-carbomethoxy-2-amino-1,2,3,4-tetrahydronaphthalene (cis-trans mixture, 10:1, 150 mg), 5-chloroindole-2-carboxylic acid (143 mg) and 1-hydroxy-7-azabenzotriazole (119 mg) in tetrahydrofuran (20 mL) at room temperature under argon, was added 1-[3-dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride (167 mg). After 16 h, the reaction mixture was diluted with ethyl acetate. The organic layer was washed sequentially with 1.0 M aqueous hydrochloric acid solution (20 mL), 1.0 M aqueous sodium hydroxide solution (20 mL) and brine (20 mL), dried over anhydrous magnesium sulfate and evaporated under vacuum to obtain crude product (243 mg) as an oil. The crude product was purified by reverse phase preparative HPLC to obtain cis 1-carbomethoxy-2-(5-chloroindole-2-carbonylamino)-1,2,3,4-tetrahydronaphthalene (167 mg) and trans 1-carbomethoxy-2-(5-chloroindole-2-carbonylamino)-1,2,3,4-tetrahydronaphthalene (14 mg).

Provenance & Evidence