反应详情

A mixture of 7-(2-methoxyethoxy)-4-(2-methyl-3-(4-oxoquinazolin-3(4H)-yl)phenyl)-9H-pyrido[3,4-b]indole-1-carboxamide (70 mg, 0.135 mmol) and aluminum triiodide (137 mg, 0.337 mmol) in acetonitrile (6 mL) was heated at reflux for 4 hr. Upon cooling to room temperature, the reaction was quenched with ice water (20 mL). The mixture was extracted with ethyl acetate (3×30 mL). The combined extract was with brine (25 mL) and dried over anhydrous MgSO4. After the solvent was removed under vacuum, the residue was purified by reverse phase HPLC. The correct fractions were concentrated under vacuum, basified with saturated NaHCO3 solution, and extracted with ethyl acetate (3×30 mL). The combined extract was washed with brine (30 mL) and dried over anhydrous MgSO4. Removal of solvent under vacuum provided the desired product (12.9 mg, 0.026 mmol, 19.54% yield) as a yellow solid. LCMS (M+H)+=462.23. 1H NMR (500 MHz, DMSO-d6) (recognizable peaks for the major atropisomer) δ: 11.56 (s, 1H), 9.84 (s, 1H), 8.16 (s, 1H), 7.19 (s, 1H), 7.16 (d, J=8.6 Hz, 1H), 1.81 (s, 3H).

1. temperaturewas heated
2. temperatureat reflux for 4 hr
3. customthe reaction was quenched with ice water (20 mL)
4. extractionThe mixture was extracted with ethyl acetate (3×30 mL)
5. extractionThe combined extract
6. dry with materialdried over anhydrous MgSO4
7. customAfter the solvent was removed under vacuum
8. customthe residue was purified by reverse phase HPLC
9. concentrationThe correct fractions were concentrated under vacuum
10. extractionextracted with ethyl acetate (3×30 mL)
11. extractionThe combined extract
12. washwas washed with brine (30 mL)
13. dry with materialdried over anhydrous MgSO4
14. customRemoval of solvent under vacuum