Acetic Acid → HCID 178489372, compound

Temperature

70 °C

To a solution of 5-bromo-3-(2-methoxy-phenyl)-1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrazolo[3,4-b]pyridine (260 mg, 0.60 mmol) in THF (3 mL) was added tetrabutylammonium fluoride (6 mL of 1 M in THF solution, 6.00 mmol) and molecular sieves. The solution was heated under reflux (70° C.) for 4 hours without stirring. The solution was cooled to ambient temperature and acidified to pH=5 by adding dropwise a dilute solution of acetic acid in MeOH. The solution was filtered and the filtrate was concentrated via rotary evaporation. The material was extracted into EtOAc and washed 3×H2O. The organic layer was dried over Na2SO4 and concentrated down to afford 5-bromo-3-(2-methoxy-phenyl)-1H-pyrazolo[3,4-b]pyridine as an orange solid (177 mg, 97% yield). MS: m/z 303.9, 305.9 [M+H+]. The material was used directly in step 2 without further purification.

1. temperatureThe solution was heated
2. temperatureThe solution was cooled to ambient temperature
3. filtrationThe solution was filtered
4. concentrationthe filtrate was concentrated via rotary evaporation
5. extractionThe material was extracted into EtOAc
6. washwashed 3×H2O
7. dry with materialThe organic layer was dried over Na2SO4
8. concentrationconcentrated down

ORD record

ord-c59327663e77453189bd64494105215f

Source dataset

uspto-grants-2010_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07829558B2