Cesium carbonate → Tert-butyl 1H-pyrazolo[4,3-b]pyridin-1-ylacetate

HRID 82232Notes

Reaction equation

HRID 82232 reaction equation
Br[CH2:2][C:3]([O:5][C:6]([CH3:9])([CH3:8])[CH3:7])=[O:4].[NH:10]1[C:18]2[C:13](=[N:14][CH:15]=[CH:16][CH:17]=2)[CH:12]=[N:11]1.C([O-])([O-])=O.[Cs+].[Cs+]>CN(C=O)C.C(OCC)(=O)C>[N:10]1([CH2:2][C:3]([O:5][C:6]([CH3:9])([CH3:8])[CH3:7])=[O:4])[C:18]2[C:13](=[N:14][CH:15]=[CH:16][CH:17]=2)[CH:12]=[N:11]1

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 79177tert-Butyl bromoacetateHCID 216436531H-Pyrazolo(4,3-b)pyridine

Product 1

HCID 70817224Tert-butyl 1H-pyrazolo[4,3-b]pyridin-1-ylacetateYield 51%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

Tert-butyl bromoacetate (0.55 mL, 3.69 mmol) was added to 1H-pyrazolo[4,3-b]pyridine (220 mg, 1.85 mmol) and Cs2CO3 (723 mg, 2.22 mmol) in anhydrous DMF (7 mL). The mixture was stirred at room temperature for 1 hour. The reaction mixture was diluted with ethyl acetate (50 mL), washed with water (3×30 mL), brine (30 mL), dried over sodium sulphate, evaporated in vacuo and purified by column chromatography on silica gel (hexane:EtOAc 80:20) to afford a colourless gum in 51% yield, 220 mg.

Workup

  1. washwashed with water (3×30 mL), brine (30 mL)
  2. dry with materialdried over sodium sulphate
  3. customevaporated in vacuo
  4. custompurified by column chromatography on silica gel (hexane:EtOAc 80:20)
  5. customto afford a colourless gum in 51% yield, 220 mg

Sources & evidence

ORD record
ord-ae5d1418ad584a08b49afb2ae6df6750
Source dataset
uspto-grants-2014_09
Patent number
US08846698B2

Reaction notes

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