反应详情

温度

80 °C

To a solution of ethyl 2-amino-3-(4-bromo-7-carbamoyl-1H-indol-3-yl)propanoate (3.45 g, 9.74 mmol) in methanol (68.8 mL) and 1 M aqueous HCl (52.9 mL) was added 37% aqueous formaldehyde (0.790 mL, 9.74 mmol) and the resulting mixture was heated at 80° C. After 1.5 h, additional formaldehyde (0.79 mL) was added and heating was continued. After 3.5 h, additional formaldehyde (0.79 mL) was again added and heating was continued. After 6 h, the mixture was cooled to room temperature, concentrated, and partitioned between a solvent mixture of CHCl3 and iPrOH (3:1) and 1 M NaOH and NaHCO3 (aq). The organic phase was washed with brine, dried and concentrated to afford the crude product as a light brown solid (3.16 g, 89% yield). LCMS (M+H)+ m/z 365.8, 367.8.

1. temperatureheating
2. waitAfter 3.5 h
3. temperatureheating
4. waitAfter 6 h
5. temperaturethe mixture was cooled to room temperature
6. concentrationconcentrated
7. custompartitioned between a solvent mixture of CHCl3 and iPrOH (3:1) and 1 M NaOH and NaHCO3 (aq)
8. washThe organic phase was washed with brine
9. customdried
10. concentrationconcentrated