3-Pyridinemethanol → HCID 67402243, compound

HRID 1186316Notes

Reaction equation

HRID 1186316 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH2:7][OH:8])[CH:2]=1.[H-].[Na+].[NH2:11][C:12]1[C:21](Cl)=[N:20][C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[N:13]=1.[Cl-].[NH4+]>O1CCCC1.C(OCC)(=O)C>[NH2:11][C:12]1[C:21]([O:8][CH2:7][C:3]2[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=2)=[N:20][C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[N:13]=1

Participants

7

Reactant 4

HCID 75103-PyridinemethanolHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 8172743-Chloroquinoxalin-2-amine

Product 1

HCID 67402243HCID 67402243, compoundYield 91%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

3-Pyridinemethanol (487 μL, 5.01 mmol) was dissolved in tetrahydrofuran (6.0 mL). To this, 60% sodium hydride (in oil) (200 mg, 5.01 mmol) was added under a nitrogen atmosphere at 0° C. and the mixture was stirred at the same temperature for 15 minutes. To this, 2-amino-3-chloroquinoxaline (300 mg, 1.67 mmol) was added and the mixture was stirred at room temperature for 14 hours. Then, a saturated aqueous ammonium chloride solution was added to the reaction mixture, and extraction with ethyl acetate was performed, followed by washing with brine and drying over anhydrous sodium sulfate. The solvent was evaporated off under reduced pressure, and the residue was purified by silica gel column chromatography (chloroform/methanol=9/1). Further, slurry purification was performed using diisopropyl ether, to give 2-amino-3-[(pyridin-3-yl)methoxy]quinoxaline (Compound BA) (383 mg, yield: 91%).

Workup

  1. stirringthe mixture was stirred at room temperature for 14 hours
  2. washby washing with brine
  3. dry with materialdrying over anhydrous sodium sulfate
  4. customThe solvent was evaporated off under reduced pressure
  5. customthe residue was purified by silica gel column chromatography (chloroform/methanol=9/1)
  6. customFurther, slurry purification

Sources & evidence

ORD record
ord-b531c965f7c64bf8b6c1876f3153932a
Source dataset
uspto-grants-2014_03
Patent number
US08673908B2

Reaction notes

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