Methyl iodide → HCID 90416413, compound

HRID 633563Notes

Reaction equation

HRID 633563 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[CH:11]=[CH:10][NH:9][C:5]2=[C:6]([Cl:8])[N:7]=1.[H-].[Na+].I[CH3:15]>O1CCCC1>[Br:1][C:2]1[CH:3]=[C:4]2[CH:11]=[CH:10][N:9]([CH3:15])[C:5]2=[C:6]([Cl:8])[N:7]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 467379065-Bromo-7-chloro-1H-pyrrolo[2,3-c]pyridine

Product 1

HCID 90416413HCID 90416413, compoundYield 82.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 5-bromo-7-chloro-1H-pyrrolo[2,3-c]pyridine (Aldrich, 0.86 g, 3.72 mmol) in tetrahydrofuran (37.2 mL) was treated with sodium hydride (0.297 g, 7.43 mmol) at ambient temperature, stirred for 15 minutes, treated with iodomethane (0.348 mL, 5.57 mmol), stirred for 1 hour at ambient temperature and quenched with saturated aqueous ammonium chloride. The mixture was partitioned with ethyl acetate and the organic layer was washed with saturated aqueous sodium chloride, dried (anhydrous Na2SO4), filtered, and concentrated. Purification by chromatography (silica gel, 0-40% ethyl acetate in heptanes) afforded the title compound (0.75 g, 82%).

Workup

  1. stirringstirred for 1 hour at ambient temperature
  2. customquenched with saturated aqueous ammonium chloride
  3. customThe mixture was partitioned with ethyl acetate
  4. washthe organic layer was washed with saturated aqueous sodium chloride
  5. dry with materialdried (anhydrous Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customPurification by chromatography (silica gel, 0-40% ethyl acetate in heptanes)

Sources & evidence

ORD record
ord-786fd596a5ac48e49bdfde6e9a98b5d9
Source dataset
uspto-grants-2016_04
Patent number
US09321764B2

Reaction notes

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