Potassium Carbonate → HCID 66778607, compound

HRID 2090969Notes

Reaction equation

[CH3:1][O:2][CH2:3][C:4]1[C:8]([C:9]([O:11][CH3:12])=[O:10])=[CH:7][NH:6][N:5]=1.Cl[C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([C:20]([F:23])([F:22])[F:21])[N:15]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[CH3:1][O:2][CH2:3][C:4]1[C:8]([C:9]([O:11][CH3:12])=[O:10])=[CH:7][N:6]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([C:20]([F:23])([F:22])[F:21])[N:15]=2)[N:5]=1

Participants

Conditions

Temperature: 100 °C

Procedure

To a solution of methyl 3-(methoxymethyl)-1H-pyrazole-4-carboxylate (5.1 g) synthesized in Example 29(1) in N,N-dimethylformamide (70 mL) were added 2-chloro-6-trifluoromethylpyridine (5.0 g) and potassium carbonate (6.2 g), and the mixture was stirred at 100° C. overnight. The reaction mixture was allowed to cool to room temperature and filtered through celite, water was added to the filtrate, and the mixture was extracted with diethyl ether. The extract was washed with brine, dried over magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:4, volume ratio) to give the title object compound (6.5 g, 69%) as colorless crystals.

Workup

temperatureto cool to room temperature
filtrationfiltered through celite, water
additionwas added to the filtrate
extractionthe mixture was extracted with diethyl ether
washThe extract was washed with brine
dry with materialdried over magnesium sulfate
concentrationconcentrated under reduced pressure
customThe residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:4, volume ratio)

Sources & evidence

ORD record: ord-e0ce8f98e6b44d3db58422ae65b1fbe6
Source dataset: uspto-grants-2013_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08436043B2

Reaction notes

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