Benzyl Bromide → 1-benzyl-4-chloro-3-iodo-1H-pyrazolo[4,3-c]pyridine

HRID 2206241Notes

Reaction equation

HRID 2206241 reaction equation
[Cl:1][C:2]1[C:7]2[C:8]([I:11])=[N:9][NH:10][C:6]=2[CH:5]=[CH:4][N:3]=1.[OH-].[K+].[CH2:14](Br)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C(=O)([O-])O.[Na+]>CN(C=O)C>[CH2:14]([N:10]1[C:6]2[CH:5]=[CH:4][N:3]=[C:2]([Cl:1])[C:7]=2[C:8]([I:11])=[N:9]1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

6

Reactant 4

HCID 7498Benzyl BromideHCID 14797Potassium HydroxideHCID 516892Sodium BicarbonateHCID 178478341HCID 178478341, compound

Product 1

HCID 1179879911-benzyl-4-chloro-3-iodo-1H-pyrazolo[4,3-c]pyridineYield 60%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of 4-chloro-3-iodo-1H-pyrazolo[4,3-c]pyridine (6.3 g) and potassium hydroxide (2.5 g) in DMF (60 mL) was added benzyl bromide (4.6 g) at room temperature. The reaction mixture was stirred at room temperature for 4 hr. The reaction mixture was neutralized with saturated aqueous sodium hydrogencarbonate solution under ice-cooling, and the mixture was extracted with ethyl acetate. The organic layer was washed with water and saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/petroleum ether) to give the title compound (5.0 g).

Workup

  1. temperaturecooling
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with water and saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (ethyl acetate/petroleum ether)

Sources & evidence

ORD record
ord-9e7b0c5a580340469a01ca6ecef8c7ee
Source dataset
uspto-grants-2016_06
Patent number
US09371320B2

Reaction notes

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