反应详情

A mixture of 7-(2-(2-(2-fluoroethoxy)ethoxy)ethoxy)-9H-carbazol-2-amine (95 mg, 0.28 mmol), paraformaldehyde (43 mg, 1.43 mmol), and NaOMe (492 mg, 25% MeOH solution, 2.3 mmol) in 8 mL of MeOH was heated at reflux for 1.5 h under Ar atmosphere and cooled to rt. To this mixture was added NaBH4 (54 mg, 1.43 mmol) and the mixture was heated at reflux for 2 h. After cooling to rt, the mixture was quenched onto ice. It was extracted with ether (3×30 mL) and the combined organic phase was dried over MgSO4 and concentrated. The crude product was purified with chromatography (hexane/EtOAc) to afford 7-(2-(2-(2-fluoroethoxy)ethoxy)ethoxy)-N-methyl-9H-carbazol-2-amine (AD-CB-003P-WZ0141) as a light-brown solid (55 mg, 56%).

1. temperaturewas heated
2. temperatureat reflux for 1.5 h under Ar atmosphere
3. temperaturethe mixture was heated
4. temperatureat reflux for 2 h
5. temperatureAfter cooling to rt
6. customthe mixture was quenched onto ice
7. extractionIt was extracted with ether (3×30 mL)
8. dry with materialthe combined organic phase was dried over MgSO4
9. concentrationconcentrated
10. customThe crude product was purified with chromatography (hexane/EtOAc)