反应详情

温度

0 °C

1H-pyrrolo[2,3-b]pyridin-5-amine (9.45 g, 71.05 mmol) was dissolved in THF (150 mL) and stirred at 0° C. under an atmosphere of nitrogen. Benzyl chloroformate (20.3 mL, 142.10 mmol, 2.0 Eq) was added dropwise over a period of 15 minutes and the mixture allowed to stir at room temperature for 30 minutes. The mixture was treated with 4M NaOH (aq) (53.3 mL, 213.16 mmol, 3.0 Eq) over a period of 15 minutes and the resultant brown solution left to stir for 16 hours. The reaction mixture was taken to pH 4 (125 mL of 10% aq. citric acid) and the 2 layers were separated. The aqueous layer was back extracted with EtOAc and the combined organics were dried over magnesium sulphate, filtered and dried under vacuum. The crude product was purified by column chromatography (50% EtOAc/Petroleum Ether) to give 14.59 g (77%) of pale yellow solid.

1. stirringto stir at room temperature for 30 minutes
2. waitthe resultant brown solution left
3. stirringto stir for 16 hours
4. customthe 2 layers were separated
5. extractionThe aqueous layer was back extracted with EtOAc
6. dry with materialthe combined organics were dried over magnesium sulphate
7. filtrationfiltered
8. customdried under vacuum
9. customThe crude product was purified by column chromatography (50% EtOAc/Petroleum Ether)