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Potassium Carbonate → 2,4,6-Tris(1-methyl-3-trifluoromethylpyrazol-5-yloxy)pyridine

HRID 366298
Notes
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Reaction equation

HRID 366298 reaction equation
F[C:2]1[CH:7]=[C:6](F)[CH:5]=[C:4](F)[N:3]=1.[OH:10][C:11]1[N:15]([CH3:16])[N:14]=[C:13]([C:17]([F:20])([F:19])[F:18])[CH:12]=1.[C:21](=[O:24])([O-])[O-].[K+].[K+]>S1(CCCC1)(=O)=O.CCCCC.C(OCC)(=O)C.C(OC(C)C)(C)C>[CH3:16][N:15]1[C:11]([O:10][C:2]2[CH:7]=[C:6]([O:10][C:11]3[N:15]([CH3:16])[N:14]=[C:13]([C:17]([F:20])([F:19])[F:18])[CH:12]=3)[CH:5]=[C:4]([O:24][C:21]3[N:15]([CH3:11])[N:14]=[C:13]([C:17]([F:20])([F:19])[F:18])[CH:12]=3)[N:3]=2)=[CH:12][C:13]([C:17]([F:20])([F:19])[F:18])=[N:14]1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 27832892,4,6-TrifluoropyridineHCID 178481859HCID 178481859, compound

Product 1

HCID 158696782,4,6-Tris(1-methyl-3-trifluoromethylpyrazol-5-yloxy)pyridineYield 93%

Reagents, catalysts & solvents 3

HCID 7914Diisopropyl EtherSolvent
HCID 31347
Sulfolane
Solvent
HCID 22335286Ethyl acetate pentaneSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 4.8 g (36 mmol) 2,4,6-trifluoropyridine, 19.8 g (119 mmol) 5-hydroxy-1-methyl-3-trifluoromethylpyrazole and 18.1 g (131 mmol) potassium carbonate in 25 ml anhydrous sulfolane is stirred and heated to 80° C. over a period of 3 days. After cooling, the mixture is diluted with pentane/ethyl acetate (by volume ration 1/1) and filtered through a bed of silica gel. The filtrate is washed 10 times with water and the organic layer is dried over magnesium sulfate. After removal of the solvents, the residue is washed with isopropyl ether and 19.1 g (93 % yield) colorless crystals of melting point 130 0C are obtained.

Workup

  1. temperatureAfter cooling
  2. filtrationfiltered through a bed of silica gel
  3. washThe filtrate is washed 10 times with water
  4. dry with materialthe organic layer is dried over magnesium sulfate
  5. customAfter removal of the solvents

Sources & evidence

ORD record
ord-69dddaac0574449cbcc3f0013b0a3bd9
Source dataset
uspto-grants-2000_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06130188

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes