Potassium Carbonate → HCID 67173431, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of the product of step C (100 mg, 0.27 mmol) in dimethylsulfoxide (2 mL) was added copper iodide (51 mg, 0.02 mmol), L-proline (6.2 mg, 0.05 mmol), iodobenzene (33 μL, 0.29 mmol) and potassium carbonate (75 mg, 0.54 mmol). The resulting mixture was heated to 115° C. for 40 h, diluted with water and extracted with ethyl acetate. The organic extract was dried over sodium sulfate, filtered, and concentrated in vacuo. The crude material was purified by flash chromatography (SiO2, 3:2 hexanes/ethyl acetate) to give tert-butyl 2-phenylsulfonyl-5-phenyl-5,6,7,8,9,10-hexahydro-7,10-epiminocyclohepta[b]indole-carboxylate (70 mg, 50%) as a white solid: 1H NMR (CDCl3, 300 MHz) δ 8.26 (s, 1H), 7.95-7.98 (m, 2H), 7.63 (d, J=8.7 Hz, 1H), 7.42-7.54 (m, 6H), 7.21-7.26 (m, 3H), 5.33 (br s, 1H), 4.65 (br s, 1H), 2.20-2.33 (m, 3H), 2.00-2.06 (m, 1H), 1.60-1.69 (m, 2H), 1.40 (s, 9H).

Provenance & Evidence