反应详情

A mixture of anthranilic acid (1.37 g, 1.0 mmol), 1H-pyrrolo[2,3-b]pyridine-3-carbaldehyde (1.46 g, 1.0 mmol), and p-toluenesulfonic acid mohohydrate (0.025 g, 0.13 mmol) in 30 mL of anhydrous toluene was stirred at reflux for 1 h. After being cooled to RT, NaBH4 (0.9 g) was added, and the mixture was stirred at RT for 30 min. The reaction was quenched with MeOH, and the volatiles were removed under reduced pressure. The residue was taken up in water, AcOH was added to bring pH to 4, and the mixture was extracted with EtOAc. The combined organic portions were washed with brine, dried over MgSO4, filtered, and condensed. The residue was purified by flash column chromatography to give the titled compound. MS (ES+): 268.1 (M+H)+. Calc'd for C15H13N3O2-267.10.

1. temperatureat reflux for 1 h
2. stirringthe mixture was stirred at RT for 30 min
3. customThe reaction was quenched with MeOH
4. customthe volatiles were removed under reduced pressure
5. additionAcOH was added
6. extractionthe mixture was extracted with EtOAc
7. washThe combined organic portions were washed with brine
8. dry with materialdried over MgSO4
9. filtrationfiltered
10. customcondensed
11. customThe residue was purified by flash column chromatography