Potassium Carbonate → 3-Chloro-5-difluoromethoxy-pyridine-2-carbonitrile

HRID 81620Notes

Reaction equation

HRID 81620 reaction equation
[Cl:1][C:2]1[C:3]([C:9]#[N:10])=[N:4][CH:5]=[C:6]([OH:8])[CH:7]=1.C([O-])([O-])=O.[K+].[K+].Cl[C:18]([F:23])([F:22])C([O-])=O.[Na+]>CN(C=O)C.O>[Cl:1][C:2]1[C:3]([C:9]#[N:10])=[N:4][CH:5]=[C:6]([O:8][CH:18]([F:23])[F:22])[CH:7]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 2734985Sodium chlorodifluoroacetateHCID 666654733-Chloro-5-hydroxypicolinonitrile

Product 1

HCID 666661013-Chloro-5-difluoromethoxy-pyridine-2-carbonitrile

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 3-chloro-5-hydroxy-pyridine-2-carbonitrile (314 mg, 2.03 mmol) in DMF (10 ml) was added K2CO3 (841 mg, 6.09 mmol) and sodium chlorodifluoroacetate (1.29 g, 8.11 mmol) and the reaction mixture was heated at 100° C. for 10 min. The reaction mixture was diluted with H2O and extracted with TBME. Combined extracts were washed with brine, dried over MgSO4, filtered and concentrated. The title compound was obtained as a yellow oil after chromatography on silica gel (hexane-EtOAc 20:1 to 1:1) to provide the title compound as a light yellow oil: TLC (hexane-EtOAc 2:1): Rf=0.54;

Workup

  1. extractionextracted with TBME
  2. washCombined extracts were washed with brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-48b6ee3ee799479bb28a4a8cae326931
Source dataset
uspto-grants-2014_09
Patent number
US08846658B2

Reaction notes

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