2-Bromoethyldimethylamine → HCID 57843493, compound

HRID 734985Notes

Reaction equation

HRID 734985 reaction equation
[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([N:6]=[CH:7][C:8]([C:12]3[CH:13]=[N:14][NH:15][CH:16]=3)=[N:9]2)=[CH:4][CH:3]=1.[H-].[Na+].[CH3:19][N:20]([CH3:24])[CH2:21][CH2:22]Br>CN(C)C=O>[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([N:6]=[CH:7][C:8]([C:12]3[CH:16]=[N:15][N:14]([CH2:22][CH2:21][N:20]([CH3:24])[CH3:19])[CH:13]=3)=[N:9]2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 178642-BromoethyldimethylamineHCID 24758Sodium hydrideHCID 57843361HCID 57843361, compound

Product 1

HCID 57843493HCID 57843493, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 7-bromo-2-(1H-pyrazol-4-yl)quinoxaline (0.225 g, 0.808 mmol) in dry N,N-dimethylformamide (5 mL) under a nitrogen atmosphere was added 60 wt % sodium hydride (92 mg, 2.27 mmol) portionwise. After 5 minutes of stirring with purging, 2-dimethylaminoethylbromide (0.37 g, 0.908 mmol) was added and the reaction mixture stirred at rt for 30 min, concentrated in vacuo and taken into dichloromethane. The organic solution was washed with water (2×), dried (Na2SO4), filtered and concentrated in vacuo. The residue was purified by silica gel chromatography, eluting with 0-5% methanol in ethyl acetate to furnish the title compound (0.183 g, 66% yield). ESMS m/e: 345.9; 347.8 [M]+.

Workup

  1. customwith purging
  2. stirringthe reaction mixture stirred at rt for 30 min
  3. concentrationconcentrated in vacuo
  4. washThe organic solution was washed with water (2×)
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by silica gel chromatography
  9. washeluting with 0-5% methanol in ethyl acetate

Sources & evidence

ORD record
ord-1f3608d038c8452caeaf8f97ff22fbb2
Source dataset
uspto-grants-2009_09
Patent number
US07592342B2

Reaction notes

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