Potassium Carbonate → Tert-butyl 2-(3-iodo-1H-pyrazolo[3,4-c]pyridin-1-yl)acetate

HRID 1527289Notes

Reaction equation

HRID 1527289 reaction equation
[I:1][C:2]1[C:10]2[C:5](=[CH:6][N:7]=[CH:8][CH:9]=2)[NH:4][N:3]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:18][C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20]>C(#N)C>[I:1][C:2]1[C:10]2[C:5](=[CH:6][N:7]=[CH:8][CH:9]=2)[N:4]([CH2:18][C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[N:3]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 79177tert-Butyl bromoacetateHCID 178506573HCID 178506573, compound

Product 1

HCID 68283649Tert-butyl 2-(3-iodo-1H-pyrazolo[3,4-c]pyridin-1-yl)acetate

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a suspension of 3-iodo-1H-pyrazolo[3,4-c]pyridine (6.24 g, 22.9 mmol) and potassium carbonate (7.29 g, 52.7 mmol) in acetonitrile (50 mL) was added tert-butyl bromoacetate (4.06 mL, 27.5 mmol) dropwise at RT and the resulting mixture was heated to reflux for 2 h. The mixture was cooled to RT and filtered, the solid was washed with CH3CN and the filtrate was concentrated under vacuum. The residual oil was purified by flash column chromatography on silica gel (gradient EtOAc/c-hexane 1:4, then 1:2, then 1:1). MS (LC/MS): 360.0 [M+H]+; tR (HPLC conditions k): 2.93 min.

Workup

  1. temperaturethe resulting mixture was heated
  2. temperatureto reflux for 2 h
  3. filtrationfiltered
  4. washthe solid was washed with CH3CN
  5. concentrationthe filtrate was concentrated under vacuum
  6. customThe residual oil was purified by flash column chromatography on silica gel (gradient EtOAc/c-hexane 1:4
  7. custom2.93 min.

Sources & evidence

ORD record
ord-37a68cb6bbde450bb1879d8e74d0902d
Source dataset
uspto-grants-2015_07
Patent number
US09085555B2

Reaction notes

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