Potassium Carbonate → Ethyl 5-(2,2-difluoroethoxy)-3-fluoro-pyridine-2-carboxylate

HRID 1754865Notes

Reaction equation

HRID 1754865 reaction equation
[F:1][C:2]1[C:3]([C:9]([O:11][CH2:12][CH3:13])=[O:10])=[N:4][CH:5]=[C:6](F)[CH:7]=1.[F:14][C:15]([F:18])(O)[CH3:16].C(=O)([O-])[O-:20].[K+].[K+]>C(#N)C>[F:14][CH:15]([F:18])[CH2:16][O:20][C:6]1[CH:7]=[C:2]([F:1])[C:3]([C:9]([O:11][CH2:12][CH3:13])=[O:10])=[N:4][CH:5]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 20243757DifluoroethanolHCID 46311358Ethyl 3,5-difluoropyridine-2-carboxylate

Product 1

HCID 117738010Ethyl 5-(2,2-difluoroethoxy)-3-fluoro-pyridine-2-carboxylateYield 18.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Ethyl 3,5-difluoropyridine-2-carboxylate (0.98 g, 5.24 mmol) is dissolved in acetonitrile (20 mL). Difluoroethanol (430 μL, 6.81 mmol) is added followed by potassium carbonate (1.83 g, 13.09 mmol). The solution is stirred at room temperature for 2 days then filtered and the filtrate is concentrated. The crude material is purified via silica gel chromatography eluting with a 0-25-50% ethyl acetate/hexanes gradient to give the title compound (242 mg, 18%). ES/MS (m/e): 250.0 (M+1).

Workup

  1. filtrationthen filtered
  2. concentrationthe filtrate is concentrated
  3. customThe crude material is purified via silica gel chromatography
  4. washeluting with a 0-25-50% ethyl acetate/hexanes gradient

Sources & evidence

ORD record
ord-bf0e47da9e5b48b99f91ad970e881c69
Source dataset
uspto-grants-2015_10
Patent number
US09169271B2

Reaction notes

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