Benzylamine → HCID 58136544, compound

Participants

Reaction Steps

Under argon, a solution of 1 g (2.96 mmol) of methyl 2-methyl-4-{[(trifluoromethyl)sulfonyl]oxy}-2,3-dihydro-1H-indene-2-carboxylate, 290 μl (2.66 mmol) of benzylamine, 2.41 g (7.29 mmol) of cesium carbonate, 56 mg (0.12 mmol) of 2-dicyclohexylphosphino-2′,4′,6′-triisopropylbiphenyl and 54 mg (0.059 mmol) of tris(dibenzylideneaceton)dipalladium in 50 ml of dioxane was stirred at a bath temperature of 100° C. overnight. After cooling to room temperature, the reaction mixture was filtered through kieselguhr and the residue was washed repeatedly with dioxane. The combined filtrates were concentrated to dryness under reduced pressure. The crude product obtained was purified by flash chromatography on silica gel (mobile phase cyclohexane/ethyl acetate 20:1→4:1→1:1). This gave 769 mg (2.42 mmol, 93% content, 82% of theory) of a colorless solid.

Provenance & Evidence