Water → (3-Acetyl-5-methyl-pyrazolo[3,4-c]pyridin-1-yl)-acetic acid tert-butyl ester

HRID 1527271Notes

Reaction equation

HRID 1527271 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]2[C:10]([C:11](=[O:13])[CH3:12])=[N:9][NH:8][C:5]2=[CH:6][N:7]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:21][C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23].O>CC#N>[C:25]([O:24][C:22](=[O:23])[CH2:21][N:8]1[C:5]2=[CH:6][N:7]=[C:2]([CH3:1])[CH:3]=[C:4]2[C:10]([C:11](=[O:13])[CH3:12])=[N:9]1)([CH3:28])([CH3:27])[CH3:26]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 79177tert-Butyl bromoacetateHCID 682840311-(5-Methyl-1H-pyrazolo[3,4-c]pyridin-3-yl)-ethanone

Product 1

HCID 68283035(3-Acetyl-5-methyl-pyrazolo[3,4-c]pyridin-1-yl)-acetic acid tert-butyl ester

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 1-(5-methyl-1H-pyrazolo[3,4-c]pyridin-3-yl)-ethanone (1 g, 5.71 mmol) in CH3CN (30 mL) were added potassium carbonate (1.81 g, 13.13 mmol) and tert-butyl bromoacetate (0.927 mL, 6.28 mmol). The reaction mixture was stirred at reflux for 1 h, then poured into water and extracted with EtOAc (×3). The combined organic extracts were dried (Na2SO4), filtered and concentrated. The crude residue was purified by flash column chromatography on silica gel (c-hexane/EtOAc 1:0 to 3:2). TLC, Rf (c-hexane/EtOAC 1:1)=0.25; MS (UPLC/MS): 290 [M+H]+; tR (HPLC conditions f): 1.50 min.

Workup

  1. temperatureat reflux for 1 h
  2. extractionextracted with EtOAc (×3)
  3. dry with materialThe combined organic extracts were dried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude residue was purified by flash column chromatography on silica gel (c-hexane/EtOAc 1:0 to 3:2)
  7. custom1.50 min.

Sources & evidence

ORD record
ord-1f42a8b37b3c4e7e85610af4bc7e6640
Source dataset
uspto-grants-2015_07
Patent number
US09085555B2

Reaction notes

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