Potassium Carbonate → Tert-butyl 2-(3-iodo-5-methyl-1H-pyrazolo[3,4-c]pyridin-1-yl)acetate

HRID 1527306Notes

Reaction equation

HRID 1527306 reaction equation
[I:1][C:2]1[C:10]2[C:5](=[CH:6][N:7]=[C:8]([CH3:11])[CH:9]=2)[NH:4][N:3]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:19][C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21]>C(#N)C>[I:1][C:2]1[C:10]2[C:5](=[CH:6][N:7]=[C:8]([CH3:11])[CH:9]=2)[N:4]([CH2:19][C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[N:3]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 79177tert-Butyl bromoacetateHCID 178422150HCID 178422150, compound

Product 1

HCID 68283706Tert-butyl 2-(3-iodo-5-methyl-1H-pyrazolo[3,4-c]pyridin-1-yl)acetate

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a suspension of 3-iodo-5-methyl-1H-pyrazolo[3,4-c]pyridine (1.00 g, 3.86 mmol), and potassium carbonate (1.28 g, 9.26 mmol) in acetonitrile (40 mL) was added tert-butyl bromoacetate (0.685 mL, 4.63 mmol) dropwise at RT and the resulting mixture was heated to reflux for 16 h. The mixture was cooled to RT and filtered, the solid was washed with acetonitrile and the filtrate was concentrated under vacuum. The residual oil was used directly in the next step without further purification. MS (LC/MS): 374.0 [M+H]+; tR (HPLC conditions k): 2.96 min.

Workup

  1. temperaturethe resulting mixture was heated
  2. temperatureto reflux for 16 h
  3. filtrationfiltered
  4. washthe solid was washed with acetonitrile
  5. concentrationthe filtrate was concentrated under vacuum
  6. customThe residual oil was used directly in the next step without further purification
  7. custom2.96 min.

Sources & evidence

ORD record
ord-9ffb9779d5804c4b9560d2eb625536ac
Source dataset
uspto-grants-2015_07
Patent number
US09085555B2

Reaction notes

Loading…