Pyridine → ethyl N-(6-fluoro-3-methoxyquinoxalin-2-yl)carbamate

HRID 1878185Notes

Reaction equation

HRID 1878185 reaction equation
[NH2:1][C:2]1[C:11]([O:12][CH3:13])=[N:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([F:14])[CH:8]=2)[N:3]=1.Cl[C:16]([O:18][CH2:19][CH3:20])=[O:17].N1C=CC=CC=1>ClCCl>[F:14][C:7]1[CH:8]=[C:9]2[C:4](=[CH:5][CH:6]=1)[N:3]=[C:2]([NH:1][C:16](=[O:17])[O:18][CH2:19][CH3:20])[C:11]([O:12][CH3:13])=[N:10]2

Participants

5

Reactant 3

HCID 1049PyridineHCID 10928Ethyl chloroformateHCID 69245896HCID 69245896, compound

Product 1

HCID 69243333ethyl N-(6-fluoro-3-methoxyquinoxalin-2-yl)carbamateYield 95%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-Amino-6-fluoro-3-methoxyquinoxaline (580 mg, 3.00 mmol) and ethyl chloroformate (391 mg, 3.60 mmol) were dissolved in dichloromethane (50 ml) at room temperature and thereto pyridine (285 mg, 3.60 mmol) was added. The resulting mixture was stirred at room temperature for 10 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 756 mg of the titled compound (yield, 95%).

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-990d04141d384fe2abf86a5049c83a8e
Source dataset
uspto-grants-2012_11
Patent number
US08314100B2

Reaction notes

Loading…