Potassium Carbonate → HCID 19609780, compound

HRID 1602052Notes

Reaction equation

[CH3:1][C:2]1[C:7]([F:8])=[C:6](F)[N:5]=[C:4](F)[C:3]=1[F:11].[C:12](=[O:15])([O-])[O-].[K+].[K+].[OH:18][C:19]1[N:23]([CH3:24])[N:22]=[C:21]([C:25]([F:28])([F:27])[F:26])[CH:20]=1>CN(C=O)C>[CH3:24][N:23]1[C:19]([O:18][C:6]2[C:7]([F:8])=[C:2]([CH3:1])[C:3]([F:11])=[C:4]([O:15][C:12]3[N:23]([CH3:19])[N:22]=[C:21]([C:25]([F:28])([F:27])[F:26])[CH:20]=3)[N:5]=2)=[CH:20][C:21]([C:25]([F:28])([F:27])[F:26])=[N:22]1

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of 4-methyl-2,3,5,6-tetrafluoropyridine (4 g, 24 mmol), potassium carbonate (3.7 g, 26.5 mmol) and 5-hydroxy-1-methyl-3-trifluoromethylpyrazole (4.4 g, 26.5 mmol) in anhydrous DMF (20 ml) is heated to 80° C. overnight. After cooling, the solvent is removed under reduced pressure. Pentane/ethyl acetate (1/2 by volume) is added to the residue and the mixture is washed twice with water. After drying of the organic layer, the solvent is removed and both products are purified by flash chromatography: One obtains 2-(1-methyl-3-trifluoromethylpyrazol.-5-yloxy)-4-methyl-3,5,6-trifluoropyridine (silica gel, pentane/ethyl acetate 1/1 by volume) (1.6 g, 21%) and 2,6-bis(1-methyl-3-trifluoromethylpyrazol-5-yloxy)-3,5-difluoro-4-methylpyridine (silica gel, pentane/ethyl acetate 1/1) (4.8 g, 43% yield, m.p. 101° C.).

Workup

temperatureAfter cooling
customthe solvent is removed under reduced pressure
additionPentane/ethyl acetate (1/2 by volume) is added to the residue
washthe mixture is washed twice with water
customAfter drying of the organic layer
customthe solvent is removed
customboth products are purified by flash chromatography

Sources & evidence

ORD record: ord-1ff0a48eff204a4698aafeae0f4d1c99
Source dataset: uspto-grants-1999_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05981437

Reaction notes

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