Potassium Carbonate → Methyl 5-(2,2-difluoroethoxy)-3-methylpyrazine-2-carboxylate

HRID 627704Notes

Reaction equation

HRID 627704 reaction equation
Cl[C:2]1[N:3]=[C:4]([CH3:12])[C:5]([C:8]([O:10][CH3:11])=[O:9])=[N:6][CH:7]=1.[F:13][CH:14]([F:17])[CH2:15][OH:16].C(=O)([O-])[O-].[K+].[K+]>O>[F:13][CH:14]([F:17])[CH2:15][O:16][C:2]1[N:3]=[C:4]([CH3:12])[C:5]([C:8]([O:10][CH3:11])=[O:9])=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 1361872,2-Difluoroethan-1-olHCID 72218580Methyl 5-chloro-3-methylpyrazine-2-carboxylate

Product 1

HCID 86728150Methyl 5-(2,2-difluoroethoxy)-3-methylpyrazine-2-carboxylateYield 20.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of methyl 5-chloro-3-methylpyrazine-2-carboxylate (255 mg, 1.367 mmol) in 2,2-difluoroethanol (0.52 mL, 8.20 mmol) was added potassium carbonate (227 mg, 1.640 mmol). The reaction was stirred at ambient temperature for 1.5 hrs. The reaction was treated with water and extracted with ethyl acetate. The organic portion was dried over Na2SO4, filtered, concentrated and purified by column chromatography, eluting with 0-2% MeOH/DCM to give the title compound (63.8 mg, 0.275 mmol, 20.1%). MS m/z=233.1 (M+H).

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe organic portion was dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. custompurified by column chromatography
  6. washeluting with 0-2% MeOH/DCM

Sources & evidence

ORD record
ord-268f8a4fb9ae4328941255e471e9b755
Source dataset
uspto-grants-2016_04
Patent number
US09309263B2

Reaction notes

Loading…