Water → 3-Bromo-1-cyclobutyl-1H-pyrazolo[4,3-b]pyridine

HRID 573291Notes

Reaction equation

HRID 573291 reaction equation
[Br:1][C:2]1[C:6]2=[N:7][CH:8]=[CH:9][CH:10]=[C:5]2[NH:4][N:3]=1.[CH:11]1(Br)[CH2:14][CH2:13][CH2:12]1.C([O-])([O-])=O.[Cs+].[Cs+].O>CN(C=O)C>[Br:1][C:2]1[C:6]2=[N:7][CH:8]=[CH:9][CH:10]=[C:5]2[N:4]([CH:11]2[CH2:14][CH2:13][CH2:12]2)[N:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 10796Cesium carbonateHCID 78110BromocyclobutaneHCID 178419484HCID 178419484, compound

Product 1

HCID 667280263-Bromo-1-cyclobutyl-1H-pyrazolo[4,3-b]pyridine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 3-bromo-1H-pyrazolo[4,3-b]pyridine (200 mg) in DMF (10 ml) were added cyclobutyl bromide (0.19 mL) and Cs2CO3 (395 mg) at room temperature. After stirring overnight at 60° C., the reaction mixture was poured into water and extracted with AcOEt. The extract was washed with water and brine, dried over MgSO4, and concentrated under reduced pressure. The residue was purified by basic silica gel column chromatography (AcOEt/hexane) to give the title compound (181 mg).

Workup

  1. extractionextracted with AcOEt
  2. washThe extract was washed with water and brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by basic silica gel column chromatography (AcOEt/hexane)

Sources & evidence

ORD record
ord-6d482ebb728c4c49a9327135f0f5a437
Source dataset
uspto-grants-2015_05
Patent number
US09029536B2

Reaction notes

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