Sulfate Ion → HCID 86602409, compound

HRID 2373226Notes

Reaction equation

HRID 2373226 reaction equation
[CH2:1]([N:3]1[C:7]2=[N:8][C:9]([CH2:21][O:22][CH3:23])=[C:10]([CH2:19][OH:20])[C:11]([C:12]3[CH:13]=[N:14][CH:15]=[C:16]([CH3:18])[CH:17]=3)=[C:6]2[CH:5]=[N:4]1)[CH3:2].[OH-].[Na+].S([O-])([O-])(=O)=O.Br[CH2:32][C:33]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34]>O.C1(C)C=CC=CC=1>[CH2:1]([N:3]1[C:7]2=[N:8][C:9]([CH2:21][O:22][CH3:23])=[C:10]([CH2:19][O:20][CH2:32][C:33]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34])[C:11]([C:12]3[CH:13]=[N:14][CH:15]=[C:16]([CH3:18])[CH:17]=3)=[C:6]2[CH:5]=[N:4]1)[CH3:2]

Participants

7

Reactant 4

HCID 1117Sulfate IonHCID 14798Sodium HydroxideHCID 79177tert-Butyl bromoacetateHCID 11688198HCID 11688198, compound

Product 1

HCID 86602409HCID 86602409, compoundYield 68.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

[1-Ethyl-6-(methoxymethyl)-4-(5-methyl-3-pyridyl)-1H-pyrazolo[3,4-b]pyridin-5-yl]methanol (57 mg), toluene (0.3 ml), 50% aqueous NaOH solution and tetrabutylammonim sulfate (32 mg) were stirred at room temperature. tert-Butyl bromoacetate (53 mg) was added dropwise and stirring was continued for 2 hours. Water (3 ml) was added and organic layer was separated. Water layer was extracted with EtOAc (×2). Organic layer was combined and dried over MgSO4. The solvent was evaporated to give dark brown oil. The crude compound was purified by flash column chromatography on silica gel (CHCl3:MeOH=50:1) to give tert-butyl {[1-ethyl-6-(methoxymethyl)-4-(5-methyl-3-pyridyl)-1H-pyrazolo[3,4-b]pyridin-5-yl]methoxy}acetate (53 mg) as colorless oil

Workup

  1. customorganic layer was separated
  2. extractionWater layer was extracted with EtOAc (×2)
  3. dry with materialdried over MgSO4
  4. customThe solvent was evaporated
  5. customto give dark brown oil
  6. customThe crude compound was purified by flash column chromatography on silica gel (CHCl3:MeOH=50:1)

Sources & evidence

ORD record
ord-2680d9e8c62545d6a9a8af92af0b2092
Source dataset
uspto-grants-2008_12
Patent number
US07459451B2

Reaction notes

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