Methyl Ethyl Ketone → 5-Bromo-2,3-dimethyl-1H-pyrrolo[2,3-B]pyridine

2-Butanone (715 μl) was added to a solution of 5-bromo-2-hydrazinopyridine (1000 mg) in ethanol (10 ml), and the mixture was heated under reflux for 2 hours. The reaction solution was concentrated under reduced pressure. Diethylene glycol (10 ml) was added and the mixture was heated under reflux for 23 hours. The reaction solution was concentrated under reduced pressure and separated by adding dichloromethane and distilled water. The resulting organic layer was washed with brine and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure. The resulting residue was purified by silica gel column chromatography (developed with methanol-chloroform) to give the title compound (104 mg).

1. temperaturethe mixture was heated
2. temperatureunder reflux for 2 hours
3. concentrationThe reaction solution was concentrated under reduced pressure
4. additionDiethylene glycol (10 ml) was added
5. temperaturethe mixture was heated
6. temperatureunder reflux for 23 hours
7. concentrationThe reaction solution was concentrated under reduced pressure
8. customseparated
9. additionby adding dichloromethane
10. distillationdistilled water
11. washThe resulting organic layer was washed with brine
12. dry with materialdried over anhydrous sodium sulfate
13. customThe solvent was evaporated under reduced pressure
14. customThe resulting residue was purified by silica gel column chromatography (developed with methanol-chloroform)

ORD record

ord-c9446342522846138d542b83e5547178

Source dataset

uspto-grants-2013_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08436012B2