Water → 3-bromo-1-ethyl-1H-pyrazolo[4,3-b]pyridine

HRID 573268Notes

Reaction equation

HRID 573268 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.[CH2:11](I)[CH3:12].C([O-])([O-])=O.[K+].[K+].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]([CH2:11][CH3:12])[N:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 178419484HCID 178419484, compound

Product 1

HCID 667278823-bromo-1-ethyl-1H-pyrazolo[4,3-b]pyridine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A suspension of 3-bromo-1H-pyrazolo[4,3-b]pyridine (2.22 g), EtI (1.08 mL), and K2CO3 (2.32 g) in DMF (15 mL) was stirred overnight at room temperature. 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 purified by basic silica gel column chromatography (hexane/AcOEt) and crystallized from hexane/AcOEt to give the title compound (1.90 g).

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 purified by basic silica gel column chromatography (hexane/AcOEt)
  6. customcrystallized from hexane/AcOEt

Sources & evidence

ORD record
ord-1d969468877d4f1db75c73fedcac73dd
Source dataset
uspto-grants-2015_05
Patent number
US09029536B2

Reaction notes

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