Potassium Phosphate, Tribasic → methyl 1-(4-(trifluoromethyl)phenyl)-1H-pyrazole-3-carboxylate

HRID 2194842Notes

Reaction equation

HRID 2194842 reaction equation
CN[C@H]1CCCC[C@@H]1NC.P([O-])([O-])([O-])=O.[K+].[K+].[K+].I[C:20]1[CH:25]=[CH:24][C:23]([C:26]([F:29])([F:28])[F:27])=[CH:22][CH:21]=1.[NH:30]1[CH:34]=[CH:33][C:32]([C:35]([O:37][CH3:38])=[O:36])=[N:31]1>CCOC(C)=O.[Cu](I)I.C1(C)C=CC=CC=1>[F:27][C:26]([F:29])([F:28])[C:23]1[CH:24]=[CH:25][C:20]([N:30]2[CH:34]=[CH:33][C:32]([C:35]([O:37][CH3:38])=[O:36])=[N:31]2)=[CH:21][CH:22]=1

Participants

8

Reactant 4

HCID 62657Potassium Phosphate, TribasicHCID 67993Benzene, 1-iodo-4-(trifluoromethyl)-HCID 13822957(1S,2S)-(+)-N,N'-Dimethylcyclohexane-1,2-diamineHCID 178498454HCID 178498454, compound

Product 1

HCID 67321130methyl 1-(4-(trifluoromethyl)phenyl)-1H-pyrazole-3-carboxylate

Reagents, catalysts & solvents 3

HCID 83717Copper iodideCatalystHCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
110 °C

Procedure

A 30 mL pressure tube was charged with (1S,2S)—N1,N2-dimethylcyclohexane-1,2-diamine 61 (0.41 mL, 2.6 mmol), copper iodide (361 mg, 1.9 mmol), potassium phosphate (6.1 g, 29 mmol), 1-iodo-4-(trifluoromethyl)benzene 62 (3.2 g, 12 mmol), methyl 1H-pyrazole-3-carboxylate 60 (1.5 g, 12 mmol), and 15 mL of toluene. This mixture was heated at 110° C. for 16 h. After cooling to room temperature, the mixture was diluted with EtOAc and filtered. The filtrate was concentrated onto silica and purified by flash column chromatography on silica gel (0% to 3% MeOH in DCM) to give methyl 1-(4-(trifluoromethyl)phenyl)-1H-pyrazole-3-carboxylate 63.

Workup

  1. temperatureAfter cooling to room temperature
  2. filtrationfiltered
  3. concentrationThe filtrate was concentrated onto silica
  4. custompurified by flash column chromatography on silica gel (0% to 3% MeOH in DCM)

Sources & evidence

ORD record
ord-21bb526945014f81bba5e59df2002dcf
Source dataset
uspto-grants-2012_12
Patent number
US08334317B2

Reaction notes

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