Potassium Carbonate → methyl 5-(3,5-bistrifluoromethylpyrazol-1-ylmethyl)-2-(3-chloropyridin-2-yl)-2H-pyrazole-3-carboxylate

HRID 1842540Notes

Reaction equation

[Cl:1][C:2]1[C:3]([N:8]2[C:12]([C:13]([O:15][CH3:16])=[O:14])=[CH:11][C:10]([CH2:17]OS(C)(=O)=O)=[N:9]2)=[N:4][CH:5]=[CH:6][CH:7]=1.C(=O)([O-])[O-].[K+].[K+].[F:29][C:30]([F:41])([F:40])[C:31]1[CH:35]=[C:34]([C:36]([F:39])([F:38])[F:37])[NH:33][N:32]=1>C(#N)C>[F:39][C:36]([F:37])([F:38])[C:34]1[CH:35]=[C:31]([C:30]([F:29])([F:40])[F:41])[N:32]([CH2:17][C:10]2[CH:11]=[C:12]([C:13]([O:15][CH3:16])=[O:14])[N:8]([C:3]3[C:2]([Cl:1])=[CH:7][CH:6]=[CH:5][N:4]=3)[N:9]=2)[N:33]=1

Participants

Conditions

Temperature: 60 °C

Procedure

A solution of 700 mg (2.03 mmol) of methyl 2-(3-chloropyridin-2-yl)-5-methanesulphonyloxymethyl-2H-pyrazole-3-carboxylate in 15 ml of acetonitrile is admixed in succession with 336 mg (2.43 mmol) of potassium carbonate and 413 mg (2.03 mmol) of 3,5-bis(trifluoromethyl)pyrazole and the mixture is subsequently stirred at 60° C. for 1 h. After the mixture has cooled to room temperature, the solvent is concentrated on a rotary evaporator, water is added and extraction is carried out with three times 50 ml of ethyl acetate. The combined organic phases are dried over magnesium sulphate and then the solvent is removed on a rotary evaporator.

Workup

temperatureAfter the mixture has cooled to room temperature
concentrationthe solvent is concentrated on a rotary evaporator, water
additionis added
extractionextraction
dry with materialThe combined organic phases are dried over magnesium sulphate
customthe solvent is removed on a rotary evaporator

Sources & evidence

ORD record: ord-b16e0e6205fe43ed9641d817c1defbd5
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08946236B2

Reaction notes

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