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

HRID 2229110

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

Participants

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° C. are obtained.

Workup

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

Sources & evidence

ORD record: ord-b9a85229f0c4469ba322cc2afebe7916
Source dataset: uspto-grants-2002_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06420315B1

Linked notes

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