反应详情

A solution of 2-bromo-4,6-dimethylpyridin-3-amine [104829-98-3] (4.00 g, 19.9 mmol) in acetic acid (300 mL) was treated with a solution of sodium nitrite (1.37 g, 19.9 mmol) in water (2.5 mL). The reaction mixture was stirred at RT for 15 min and was then allowed to stand at ambient temperature for 24 h. An additional solution of sodium nitrite (500 mg, 7.25 mmol) in water (1 mL) was added to the mixture which was allowed to stand at RT for 16 h. Acetic acid was evaporated under reduced pressure and the residual aqueous solution was partitioned between EtOAc and sat. aq. NaHCO3. The precipitate was filtered off, washed and discarded. The combined filtrates were washed with water and brine, then dried (Phase separator) and concentrated under vacuum to give 7-bromo-5-methyl-1H-pyrazolo[3,4-c]pyridine as a solid. MS (LC-MS): 212 [M+H]+, tR (HPLC conditions k): 2.49 min.

1. waitto stand at ambient temperature for 24 h
2. waitto stand at RT for 16 h
3. customAcetic acid was evaporated under reduced pressure
4. customthe residual aqueous solution was partitioned between EtOAc and sat. aq. NaHCO3
5. filtrationThe precipitate was filtered off
6. washwashed
7. washThe combined filtrates were washed with water and brine
8. customdried (Phase separator)
9. concentrationconcentrated under vacuum