Ammonium Hydroxide → 4-chloro-1H-pyrrolo[2,3-b]pyridine-5-carboxamide

Temperature

60 °C

To a solution of 4-chloro-1H-pyrrolo[2,3-b]pyridine-5-carboxylicacid (840 mg) in N,N-dimethylformamide (8.4 mL) were added 1-hydroxybenzotriazole (808 mg) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide (929 mg). The mixture was stirred at 60° C. for 30 minutes. The solution was cooled to ambient temperature and added 28% ammonium hydroxide aqueous solution (1.2 mL). The mixture was stirred at ambient temperature for 1 hour. To the solution were added water and chloroform and the mixture was extracted with chloroform. The extract was dried over MgSO4, filtrated and evaporated. The residue was purified by column chromatography on silica gel with chloroform and methanol (100:0 to 90:10) to give 4-chloro-1H-pyrrolo[2,3-b]pyridine-5-carboxamide (90 mg) as a pale yellow powder.

1. temperatureThe solution was cooled to ambient temperature
2. stirringThe mixture was stirred at ambient temperature for 1 hour
3. extractionthe mixture was extracted with chloroform
4. dry with materialThe extract was dried over MgSO4
5. filtrationfiltrated
6. customevaporated
7. customThe residue was purified by column chromatography on silica gel with chloroform and methanol (100:0 to 90:10)

ORD record

ord-aee9318ac9c644b2b71c36bd52d719fb

Source dataset

uspto-grants-2012_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08163767B2