反应详情

2-(2-Amino-4-bromo-phenyl)-malonic acid di-tert-butyl ester (1.93 g, 5.0 mmol) and 4-quinolinecarboxaldehyde (890 mg, 5.50 mmol) were dissolved in 20 ml of AcOH under an atmosphere of dry N2. To this solution was added 95% NaHB(OAc)3 (1.45 g, 6.5 mmol) and the solution was stirred for 30 minutes. The reaction mixture was concentrated under vacuum and then stirred in 60 ml of a 1:1 solution of DCM/water. To this mixture was slowly added NaHCO3 until the pH˜8. The DCM layer was then washed with saturated aqueous NaHCO3 and dried over Na2SO4, filtered and concentrated under vacuum to give a golden oil which was subsequently dissolved in a solution of 20 ml of TFA and 2.5 ml of triethylsilane under an atmosphere of dry N2. The mixture was stirred overnight after which time the reaction mixture was concentrated under vacuum and then partitioned between DCM and saturated aqueous NaHCO3. The DCM layer was dried over Na2SO4, filtered and concentrated under vacuum to give a brown solid which, after trituration with Et2O, gives the tilted compound as a white solid.

1. concentrationThe reaction mixture was concentrated under vacuum
2. stirringstirred in 60 ml of a 1:1 solution of DCM/water
3. washThe DCM layer was then washed with saturated aqueous NaHCO3
4. dry with materialdried over Na2SO4
5. filtrationfiltered
6. concentrationconcentrated under vacuum
7. customto give a golden oil which
8. stirringThe mixture was stirred overnight after which time the reaction mixture
9. concentrationwas concentrated under vacuum
10. custompartitioned between DCM and saturated aqueous NaHCO3
11. dry with materialThe DCM layer was dried over Na2SO4
12. filtrationfiltered
13. concentrationconcentrated under vacuum
14. customto give a brown solid which