Imidazole → HCID 58739179, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of (S)-1-(3-bromo-phenyl)-ethyl]-carbamic acid tert-butyl ester (500 mg, 1.66 mmol), imidazole (170 mg, 2.5 mmol), copper (II) triflate benzene complex (83 mg, 0.16 mmole), 1–10 phenantroline ( 300 mg, 1.66 mmole), dibenzilideneacetone (37 mg, 0.16 mmole), and cesium carbonate (595 mg, 1.86 mmole) was suspended in xylenes (1 mL) in a sealed tube. The reaction mixture was heated at 110° C. for 18 h in an oil bath and then cooled down to room temperature. Ethyl acetate (20 mL) was added, the resulting solution was washed with water (2×20 mL), and the combined organic layers were dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated in vacuo, and the crude product was dissolved in CH2Cl2 (8 mL) and trifluoroacetic acid (2 mL). The reaction mixture was stirred at room temperature for 1 h and concentrated in vacuo. The residue was purified by preparative HPLC ( NH4OAc) to give the title product (75 mg, 24% yield).

Provenance & Evidence