Ethylene Glycol → 2-((7-Bromoquinoxalin-2-yl)oxy)ethanol

HRID 2221152Notes

Reaction equation

HRID 2221152 reaction equation
[H-].[Na+].[CH2:3]([OH:6])[CH2:4][OH:5].[Br:7][C:8]1[CH:17]=[C:16]2[C:11]([N:12]=[CH:13][C:14](Cl)=[N:15]2)=[CH:10][CH:9]=1>CN(C=O)C.C(Cl)(Cl)Cl.C(O)(C)C>[Br:7][C:8]1[CH:17]=[C:16]2[C:11]([N:12]=[CH:13][C:14]([O:5][CH2:4][CH2:3][OH:6])=[N:15]2)=[CH:10][CH:9]=1

Participants

6

Reactant 3

HCID 174Ethylene GlycolHCID 24758Sodium hydrideHCID 49132537-Bromo-2-chloroquinoxaline

Product 1

HCID 597100302-((7-Bromoquinoxalin-2-yl)oxy)ethanolYield 85%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 21906603Chloroform isopropyl alcoholSolvent

Conditions

Temperature
0 °C

Procedure

Suspend sodium hydride (310 mg, 13 mmol) in a solution of ethylene glycol (800 mg, 13 mmol) in DMF (50 mL) previously cooled to 0° C. Allow the mixture to warm to room temperature and stir for 30 min. Add 7-bromo-2-chloroquinoxaline (610 mg, 2.5 mmol) and stir the resulting mixture for 2 h at room temperature. Dilute the mixture with 3:1 chloroform/isopropyl alcohol and wash the resulting solution with saturated sodium chloride solution. Dry and concentrate the organic phase in vacuo and purify the residue via silica gel chromatography to provide 564 mg (85%) of the titled compound. MS ES+ m/e 268 (M+1). 1H NMR (400 MHz, CDCl3) δ 8. (s, 1H), 8.0 (d, J=2.0 Hz, 1H), 7.90 (dd, J=8.8, 2.0 Hz, 1H), 7.7 (d, J=8.8 Hz, 1H), 4.6 (t, J=4.8 Hz, 2H), 4.39 (t, J=4.8 Hz, 2H).

Workup

  1. temperatureAllow the mixture to warm to room temperature
  2. washwash the resulting solution with saturated sodium chloride solution
  3. customDry
  4. concentrationconcentrate the organic phase in vacuo
  5. custompurify the residue via silica gel chromatography

Sources & evidence

ORD record
ord-a4889f522b0b4858975f0b7fa5b221b5
Source dataset
uspto-grants-2008_05
Patent number
US07368445B2

Reaction notes

Loading…