Potassium Iodide → 1H-Pyrrolo[2,3-b]pyridine, 4-fluoro-1-(3-methoxypropyl)-

HRID 872025Notes

Reaction equation

HRID 872025 reaction equation
[H-].[Na+].[F:3][C:4]1[CH:9]=[CH:8][N:7]=[C:6]2[NH:10][CH:11]=[CH:12][C:5]=12.Br[CH2:14][CH2:15][CH2:16][O:17][CH3:18].[I-].[K+]>CN(C)C=O>[F:3][C:4]1[CH:9]=[CH:8][N:7]=[C:6]2[N:10]([CH2:14][CH2:15][CH2:16][O:17][CH3:18])[CH:11]=[CH:12][C:5]=12

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 24758Sodium hydrideHCID 5245511-Bromo-3-methoxypropaneHCID 112979984-Fluoro-1H-pyrrolo(2,3-b)pyridine

Product 1

HCID 594942231H-Pyrrolo[2,3-b]pyridine, 4-fluoro-1-(3-methoxypropyl)-Yield 88.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

60% Oily sodium hydride (135 mg) was added to a solution of 4-fluoro-1H-pyrrolo[2,3-b]pyridine (384 mg) in N,N-dimethylformamide (6 ml) and the mixture was stirred at room temperature for 1.5 hours. 1-Bromo-3-methoxypropane (518 mg) and potassium iodide (468 mg) were added to the mixture and the reaction mixture was stirred at 50° C. for 1.5 hours. Ice water was added to the reaction mixture slowly and the mixture was extracted with ethyl acetate. The organic layer was washed with water and saturated brine successively, dried over magnesium sulfate and concentrated in vacuo. The resulted residue was purified with a silica gel column chromatography (eluting solvent: n-hexane/ethyl acetate=90/10 to 70/30) to give 4-fluoro-1-(3-methoxypropyl)-1H-pyrrolo[2,3-b]pyridine (520 mg) as a colorless oil.

Workup

  1. stirringthe reaction mixture was stirred at 50° C. for 1.5 hours
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with water and saturated brine successively
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe resulted residue was purified with a silica gel column chromatography (eluting solvent: n-hexane/ethyl acetate=90/10 to 70/30)

Sources & evidence

ORD record
ord-b911b8d18efd4b2c833c1a959c427d9c
Source dataset
uspto-grants-2015_03
Patent number
US08975252B2

Reaction notes

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