Ethyl chloroacetate → Ethyl (3-iodo-1H-pyrazolo[3,4-b]pyridin-1-yl)acetate

HRID 930580Notes

Reaction equation

HRID 930580 reaction equation
[I:1][C:2]1[C:10]2[C:5](=[N:6][CH:7]=[CH:8][CH:9]=2)[NH:4][N:3]=1.C(=O)([O-])[O-].[K+].[K+].Cl[CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20]>CN(C=O)C.C(OCC)(=O)C>[I:1][C:2]1[C:10]2[C:5](=[N:6][CH:7]=[CH:8][CH:9]=2)[N:4]([CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20])[N:3]=1

Participants

6

Reactant 3

HCID 7751Ethyl chloroacetateHCID 11430Potassium CarbonateHCID 178506575HCID 178506575, compound

Product 1

HCID 57642768Ethyl (3-iodo-1H-pyrazolo[3,4-b]pyridin-1-yl)acetateYield 83.1%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of 3-iodo-1H-pyrazolo[3,4-b]pyridine (9.8 g, 40 mmol, 1 equiv) and potassium carbonate (27.6 g, 5 equiv) in 15 mL of DMF at 90° C. was added ethyl chloroacetate (8.5 mL, 40 mmol, 1 equiv). Two hours later, the reaction mixture was diluted with ethyl acetate followed by washing with saturated aqueous NaHCO3. The organic layer was dried and concentrated to provide the crude product. Purification of the crude product by flash chromatography gave ethyl (3-Iodo-pyrazolo[3,4-b]pyridin-1-yl)-acetate (11 g).

Workup

  1. washby washing with saturated aqueous NaHCO3
  2. customThe organic layer was dried
  3. concentrationconcentrated
  4. customto provide the crude product
  5. customPurification of the crude product by flash chromatography

Sources & evidence

ORD record
ord-e2ba9675b24a4a0f93f7e0cbfc5d60ca
Source dataset
uspto-grants-2016_03
Patent number
US09296740B2

Reaction notes

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