Imidazole → HCID 74931512, compound

Participants

Reaction Conditions

Reaction Steps

A solution of racemic(2′R, 3R, 4′S)-6-chloro-4′-(3-chlorophenyl)-2′-(5-chloro-2-iodophenyl)spiro[3H-indole-3,3′-piperidine]-2,6′(1H)-dione (0.3 g, 0.5 mmol) in anhydrous N,N-dimethylformamide (10 mL) was added Cs2CO3 (1.2 g, 4 mmol) (Aldrich), CuI (95 mg, 0.5 mmol) (Aldrich), N,N,N′,N′-tetramethylethylenediamine (0.2 mL, 2 mmol), and imidazole (80 mg, 1 mmol). The mixture was heated under nitrogen at 170° C. for 0.5 h. The mixture was cooled to room temperature, partitioned between ethyl acetate and water. The organic layer was separated, and the aqueous layer was extracted with ethyl acetate. The organic layers were combined, washed with brine, dried over MgSO4, and concentrated. The residue was purified by chromatography (EtOAc:MeOH=9: 1) to give a crude product 997 mg), which was further purified by RP-HPLC to give racemic(2′R, 3R, 4′S)-6-chloro-2′-(5-chloro-2-imidazol-1-yl-phenyl)-4′-(3-chlorophenyl)spiro[3H-indole-3,3′-piperidine]-2,6′(1H)-dione as a white solid (Yield 16 mg).

Provenance & Evidence