Methyl iodide → 5-Bromo-1-methyl-1H-pyrrolo[2,3-b]pyridine

HRID 241037Notes

Reaction equation

HRID 241037 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[CH:10]=[CH:9][NH:8][C:5]2=[N:6][CH:7]=1.[H-].[Na+].I[CH3:14]>O1CCCC1>[Br:1][C:2]1[CH:3]=[C:4]2[CH:10]=[CH:9][N:8]([CH3:14])[C:5]2=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 103079325-bromo-1H-pyrrolo[2,3-b]pyridine

Product 1

HCID 152962695-Bromo-1-methyl-1H-pyrrolo[2,3-b]pyridine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of 5-bromo-1H-pyrrolo[2,3-b]pyridine (207 mg, 1.05 mmol), sodium hydride (29 mg, 1.21 mmol) in tetrahydrofuran (5 mL) was added iodomethane (164 mg, 1.15 mol) then stirred for 2 h at room temperature. The reaction mixture was carefully quenched with water then extracted with ethyl acetate (3×). The combined organic layers were dried over magnesium sulfate, filtered and concentrated under reduced pressure. The crude product was purified by silica gel chromatography to give 5-bromo-1-methyl-1H-pyrrolo[2,3-b]pyridine. MS (EI) for C8H7BrN2: 209, 211 (MH+, Br pattern).

Workup

  1. customThe reaction mixture was carefully quenched with water
  2. extractionthen extracted with ethyl acetate (3×)
  3. dry with materialThe combined organic layers were dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe crude product was purified by silica gel chromatography

Sources & evidence

ORD record
ord-acc809a3466e4a63b03bad77234f5dd5
Source dataset
uspto-grants-2014_02
Patent number
US08648066B2

Reaction notes

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