反应详情

温度

100 °C

A mixture of 5-bromoindole (500 mg; 2.55 mmol) and cuprous cyanide (342 mg; 3.83 mmol) in NMP (10 mL) was heated under microwave irradiations to 100° C. for 30 minutes then at 200° C. for 30 minutes. The reaction mixture was partitioned with water and DCM and the organic layer was washed with brine and concentrated in vacuo to give a pink solid. Purification by silica column chromatography (DCM) gave a white solid. It was dissolved in DMF (5 mL) and K2CO3 (704 mg; 5.10 mmol) and iodomethane (543 mg; 3.83 mmol) were successively added. The reaction mixture was stirred at RT for 3 days and then partitioned between water and EtOAc. The organic layer was washed with brine, dried over MgSO4 and concentrated under vacuum to give a slightly yellow oil which crystallized upon standing to give the title compound as an off-white solid (80 mg, 70%). LC/MS (Method A): 156.9 (M+H)+.

1. customThe reaction mixture was partitioned with water and DCM
2. washthe organic layer was washed with brine
3. concentrationconcentrated in vacuo
4. customto give a pink solid
5. customPurification by silica column chromatography (DCM)
6. customgave a white solid
7. custompartitioned between water and EtOAc
8. washThe organic layer was washed with brine
9. dry with materialdried over MgSO4
10. concentrationconcentrated under vacuum
11. customto give a slightly yellow oil which
12. customcrystallized