Pyridine → Ethyl N-(6,7-difluoro-2-methoxyquinoxalin-3-yl)carbamate

HRID 1878275Notes

Reaction equation

HRID 1878275 reaction equation
[NH2:1][C:2]1[C:11]([O:12][CH3:13])=[N:10][C:9]2[C:4](=[CH:5][C:6]([F:15])=[C:7]([F:14])[CH:8]=2)[N:3]=1.Cl[C:17]([O:19][CH2:20][CH3:21])=[O:18].N1C=CC=CC=1>ClCCl>[F:15][C:6]1[CH:5]=[C:4]2[C:9](=[CH:8][C:7]=1[F:14])[N:10]=[C:11]([O:12][CH3:13])[C:2]([NH:1][C:17](=[O:18])[O:19][CH2:20][CH3:21])=[N:3]2

Participants

5

Reactant 3

HCID 1049PyridineHCID 10928Ethyl chloroformateHCID 692404792-Amino-6,7-difluoro-3-methoxyquinoxaline

Product 1

HCID 69244192Ethyl N-(6,7-difluoro-2-methoxyquinoxalin-3-yl)carbamateYield 60%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-Amino-6,7-di fluoro-3-methoxyquinoxaline (550 mg, 2.60 mmol) and ethyl chloroformate (564 mg, 5.20 mmol) were dissolved in dichloromethane (50 ml) at room temperature and thereto pyridine (411 mg, 5.20 mmol) was added. The mixture was stirred at room temperature for 13 hours and concentrated under the reduced pressure to remove the solvent, and purified by SiO2 column chromatography. Extraction of the residue with a n-hexane:ethyl acetate (3:1) mixture and concentration gave 440 mg of the titled compound (yield, 60%).

Workup

  1. concentrationconcentrated under the reduced pressure
  2. customto remove the solvent
  3. custompurified by SiO2 column chromatography
  4. extractionExtraction of the residue
  5. concentrationwith a n-hexane:ethyl acetate (3:1) mixture and concentration

Sources & evidence

ORD record
ord-509dbdddee3943ba83f309a6e17277ac
Source dataset
uspto-grants-2012_11
Patent number
US08314100B2

Reaction notes

Loading…