Methyl iodide → 6-Bromo-1-methyl-1H-pyrazolo(4,3-b)pyridine

HRID 879296Notes

Reaction equation

HRID 879296 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[NH:10][N:9]=[CH:8][C:5]2=[N:6][CH:7]=1.[C:11](=O)([O-])[O-].[Cs+].[Cs+].IC>CN(C=O)C>[Br:1][C:2]1[CH:3]=[C:4]2[N:10]([CH3:11])[N:9]=[CH:8][C:5]2=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 10796Cesium carbonateHCID 401522596-Bromo-1H-pyrazolo[4,3-b]pyridine

Product 1

HCID 401522616-Bromo-1-methyl-1H-pyrazolo(4,3-b)pyridine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 6-bromo-1H-pyrazolo[4,3-b]pyridine (200 mg, 1.01 mmol) in DMF (5 mL) was added cesium carbonate (494 mg, 1.515 mmol). The reaction solution was stirred at room temperature for 5 minutes, iodomethane (215 mg, 1.515 mmol) was added. The reaction solution was stirred for 2 h and quenched with water. Volatiles were removed and the residue partitioned between ethyl acetate and water. The organic phase was washed with brine, dried (MgSO4), filtered and concentrated to give crude product which was purified by chromatographic column to afford the desired product 6-bromo-1-methyl-1H-pyrazolo[4,3-b]pyridine. LCMS-ESI+: calc'd for C7H6BrN3: 211.98 (M+H+); Found: 212.1 (M+H+).

Workup

  1. stirringThe reaction solution was stirred for 2 h
  2. customquenched with water
  3. customVolatiles were removed
  4. customthe residue partitioned between ethyl acetate and water
  5. washThe organic phase was washed with brine
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customto give crude product which
  10. customwas purified by chromatographic column

Sources & evidence

ORD record
ord-ae6a7debd9ff440ab21e22edd6428dfe
Source dataset
uspto-grants-2015_03
Patent number
US08987250B2

Reaction notes

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