Methyl iodide → 6-bromo-1,3-dimethyl-1H-pyrrolo[2,3-b]pyridine

HRID 879391Notes

Reaction equation

HRID 879391 reaction equation
[Br:1][C:2]1[N:7]=[C:6]2[NH:8][CH:9]=[C:10]([CH3:11])[C:5]2=[CH:4][CH:3]=1.[C:12](=O)([O-])[O-].[Cs+].[Cs+].IC>CN(C=O)C>[Br:1][C:2]1[N:7]=[C:6]2[N:8]([CH3:12])[CH:9]=[C:10]([CH3:11])[C:5]2=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 10796Cesium carbonateHCID 580865436-bromo-3-methyl-1H-pyrrolo[2,3-b]pyridine

Product 1

HCID 867001976-bromo-1,3-dimethyl-1H-pyrrolo[2,3-b]pyridine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 6-bromo-3-methyl-1H-pyrrolo[2,3-b]pyridine (250 mg, 1.18 mmol) in DMF (6 mL) was added cesium carbonate (502 mg, 1.54 mmol). The reaction solution was stirred at room temperature for 5 minutes, then iodomethane (219 mg, 1.54 mmol) was added. The reaction solution was stirred for 30 minutes and quenched with water. The mixture was concentrated in vacuo and the residue partitioned between ethyl acetate and water. The organic phase was washed with brine, dried (MgSO4) and concentrated to give crude which was purified by chromatographic column to afford the desired product. LCMS-ESI+: calc'd for C9H9BrN2 225.2 (M+H+); Found: 225.2 (M+H+).

Workup

  1. stirringThe reaction solution was stirred for 30 minutes
  2. customquenched with water
  3. concentrationThe mixture was concentrated in vacuo
  4. customthe residue partitioned between ethyl acetate and water
  5. washThe organic phase was washed with brine
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated
  8. customto give crude which
  9. customwas purified by chromatographic column

Sources & evidence

ORD record
ord-7c840569beef45c1ad2ac0adf24b0405
Source dataset
uspto-grants-2015_03
Patent number
US08987250B2

Reaction notes

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