Sodium Iodide → HCID 23157260, compound

HRID 2110863Notes

Reaction equation

HRID 2110863 reaction equation
[H-].[Na+].[Br:3][C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[NH:6][C:5]=1[CH3:13].[CH2:14]([O:16][CH2:17][CH2:18]Br)[CH3:15].[I-].[Na+]>CN(C)C=O>[Br:3][C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[N:6]([CH2:15][CH2:14][O:16][CH2:17][CH3:18])[C:5]=1[CH3:13]

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 24758Sodium hydrideHCID 611412-Bromoethyl ethyl etherHCID 133577413-Bromo-2-methyl-1H-indole

Product 1

HCID 23157260HCID 23157260, compoundYield 74.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Under ice-cooling, sodium hydride (60% in oil, 1.44 g, 36.0 mmol) was added to a solution of 3-bromo-2-methyl-1H-indole (6.30 g, 30.0 mmol) in N,N-dimethylformamide (30 mL) by small portions, and the mixture was stirred under a nitrogen atmosphere at the same temperature for 1 hr. 2-Bromoethyl ethyl ether (5.07 mL, 45.0 mmol) and sodium iodide (0.747 g, 4.50 mmol) were added to the reaction mixture, and the mixture was stirred at 70° C. for 6 hr. The reaction mixture was concentrated under reduced pressure, water was added and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane-25% ethyl acetate/hexane) to give the title compound (6.30 g, yield 74%) as a dark-purple oil. MS m/z 282 (MH+).

Workup

  1. temperatureUnder ice-cooling
  2. stirringthe mixture was stirred at 70° C. for 6 hr
  3. concentrationThe reaction mixture was concentrated under reduced pressure, water
  4. additionwas added
  5. extractionthe mixture was extracted with ethyl acetate
  6. washThe extract was washed with saturated brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was purified by silica gel column chromatography (hexane-25% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-11f37e02c6f64749a3d24b0c639af88f
Source dataset
uspto-grants-2009_04
Patent number
US07517910B2

Reaction notes

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