反应详情

A mixture of 6-aminoindane-5-carbonitrile (48.5 mg, 0.307 mmol), isoamyl nitrite (82 μL, 0.614 mmol) and iodide (85.7 mg, 0.338 mmol) was stirred at room temperature for 0.5 h. The mixture was then heated at 80° C. under N2 for 2 h. The reaction mixture was quenched with saturated Na2S2O3 and partitioned between dichloromethane and water. The organic layer was dried (Na2SO4) and concentrated in vacuo. The residue was purified by flash chromatography (Si, 1% EtOAc in hexanes) to yield 6-iodoindane-5-carbonitrile (39.7 mg, 50%). LCMS calc.=268.97; found=270.0 (M+1)+. 1H NMR (500 MHz, CDCl3) δ 7.78 (s, 1H), 7.48 (s, 1H), 2.96 (t, J=7.5 Hz, 2H), 2.92 (t, J=7.5 Hz, 2H), 2.16-2.10 (m, 2H).

1. temperatureThe mixture was then heated at 80° C. under N2 for 2 h
2. customThe reaction mixture was quenched with saturated Na2S2O3
3. custompartitioned between dichloromethane and water
4. dry with materialThe organic layer was dried (Na2SO4)
5. concentrationconcentrated in vacuo
6. customThe residue was purified by flash chromatography (Si, 1% EtOAc in hexanes)