Potassium Carbonate → 5-(Difluoromethoxy)-3-methylpicolinonitrile

HRID 221789Notes

Reaction equation

HRID 221789 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH3:10])[C:5]([C:8]#[N:9])=[N:6][CH:7]=1.Cl[C:12]([F:17])([F:16])C([O-])=O.[Na+].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.CCOC(C)=O>[F:16][CH:12]([F:17])[O:1][C:2]1[CH:3]=[C:4]([CH3:10])[C:5]([C:8]#[N:9])=[N:6][CH:7]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 2734985Sodium chlorodifluoroacetateHCID 299497345-Hydroxy-3-methylpyridine-2-carbonitrile

Product 1

HCID 666659915-(Difluoromethoxy)-3-methylpicolinonitrile

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 5-hydroxy-3-methyl-pyridine-2-carbonitrile (CAS registry 228867-86-5) (228 mg, 1.70 mmol), sodium chlorodifluoroacetate (CAS registry 1895-39-2) (518 mg, 3.40 mmol) and K2CO3 (705 mg, 5.10 mmol) in DMF (7 ml) was stirred for 0.5 h at 100° C. The reaction mixture was diluted with EtOAc and washed with saturated aqueous NH4Cl soln. and brine. The aqueous layers were reextracted with EtOAc, the combined organic layers dried over Na2SO4, filtrated and the filtrate was concentrated. The title compound was obtained as a colourless oil after flash chromatography on silica gel (cyclohexane/EtOAc gradient 0-3 min 95:5, 3-35 min 95:5 to 60:40).

Workup

  1. washwashed with saturated aqueous NH4Cl soln
  2. dry with materialthe combined organic layers dried over Na2SO4
  3. filtrationfiltrated
  4. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-40aba98eb1c0452f8f7cd62cf4e48346
Source dataset
uspto-grants-2012_06
Patent number
US08207164B2

Reaction notes

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