N-Iodosuccinimide → HCID 178478277, compound

Temperature

50 °C

A mixture of 5-chloro-1H-pyrazolo[3,4-b]pyridine, 30, (6.15 g, 40.10 mmol) and N-iodosuccinimide (9.46 g, 42.1 mmol) in DCE was heated to 50° C. overnight. After 16H, the reaction was cooled to room temperature and stirred overnight for 48 hr. An additional 0.20 equivalent of N-iodosuccinimide (1.80 g, 8.01 mmol) was added and the mixture was heated overnight. Then, the mixture was cooled, diluted with Et2O, washed with aq. NaHCO3, sodium thiosulfate solution, water and brine. The aqueous initial wash was back extracted with EtOAc. The combined organic layers were washed with brine, dried over Na2SO4, filtered through silica and concentrated in vacuo. Trituration of the resulting solid with minimal amounts of dichloromethane and Et2O provided the desired product as an off white solid. (2.02 g, 96% yield) in sufficient purity for use in the next reaction: 1H NMR (300 MHz, CDCl3) δ 11.28 (s, 1H), 8.55 (d, J=2.2 Hz, 1H) and 7.86 (d, J=2.2 Hz, 1H) ppm; LC/MS Gradient 10-90%, 0.1% formic 5 min, C18/ACN, RT=2.76 min, (M+H) 280.06.

1. temperatureAfter 16H, the reaction was cooled to room temperature
2. temperaturethe mixture was heated overnight
3. temperatureThen, the mixture was cooled
4. washwashed with aq. NaHCO3, sodium thiosulfate solution, water and brine
5. washThe aqueous initial wash
6. extractionwas back extracted with EtOAc
7. washThe combined organic layers were washed with brine
8. dry with materialdried over Na2SO4
9. filtrationfiltered through silica
10. concentrationconcentrated in vacuo

ORD record

ord-2f3720948e754c77b3484a36b2cff02d

Source dataset

uspto-grants-2014_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08871774B2