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Sodium Iodide → Ethyl 2-(3-(trifluoromethyl)-1H-pyrazol-1-yl)acetate

HRID 1477598
Notes
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Reaction equation

HRID 1477598 reaction equation
[F:1][C:2]([F:9])([F:8])[C:3]1[CH:7]=[CH:6][NH:5][N:4]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19].[I-].[Na+].Cl.C(N=C=NCCCN(C)C)C.ON1C2C=CC=CC=2N=N1>C(Cl)(Cl)Cl.O.C(O)C>[F:1][C:2]([F:9])([F:8])[C:3]1[CH:7]=[CH:6][N:5]([CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19])[N:4]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

10

Reactant 6

HCID 5238Sodium IodideHCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 757711-HydroxybenzotriazoleHCID 18070343-(Trifluoromethyl)pyrazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 2064143
Ethyl 2-(3-(trifluoromethyl)-1H-pyrazol-1-yl)acetate

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 6212ChloroformSolvent2×

Procedure

To a chloroform solution (2 mL) of 3-(trifluoromethyl)-1H-pyrazole (68 mg, 0.50 mmol), potassium carbonate (104 mg, 0.75 mmol) and ethyl bromoacetate (100 mg, 0.60 mmol) were added and the resultant mixture was stirred at 70° C. for 2 hours. To the reaction solution, adequate amount of sodium iodide was added and the resultant mixture was further stirred for 1 day. To the reaction solution, 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (147 mg, 0.77 mmol), 1-hydroxybenzotriazole (catalytic amount) and ethanol (500 μL) were added and the resultant mixture was stirred for 2 hours. After completion of the reaction, water was added to the reaction solution and extraction with chloroform from the resultant mixture was performed. The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure to obtain a crude product of the title compound. The crude product was used in the next reaction as it was.

Workup

  1. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  2. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-c0ab7cc382e44ff9a758c647329e5b2b
Source dataset
uspto-grants-2016_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09403798B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes