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Water → N-[2-[3-chloro-5-(3,3-dimethyl-1-butynyl)pyridin-2-yl]-2-(isopropoxyimino)ethyl]-2-(trifluoromethyl)benzamide

HRID 56056
Notes
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Reaction equation

HRID 56056 reaction equation
Br[C:2]1[CH:3]=[C:4]([Cl:28])[C:5]([C:8](=[N:23][O:24][CH:25]([CH3:27])[CH3:26])[CH2:9][NH:10][C:11](=[O:22])[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[C:18]([F:21])([F:20])[F:19])=[N:6][CH:7]=1.[CH3:29][C:30]([CH3:34])([CH3:33])[C:31]#[CH:32].O>C(N(CC)CC)C.[Cu]I>[Cl:28][C:4]1[C:5]([C:8](=[N:23][O:24][CH:25]([CH3:27])[CH3:26])[CH2:9][NH:10][C:11](=[O:22])[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[C:18]([F:21])([F:20])[F:19])=[N:6][CH:7]=[C:2]([C:32]#[C:31][C:30]([CH3:34])([CH3:33])[CH3:29])[CH:3]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 962WaterHCID 135123,3-Dimethyl-1-butyneHCID 131736909N-[2-(5-bromo-3-chloropyridin-2-yl)-2-(isopropoxyimino)ethyl]-2-(trifluoromethyl)benzamide

Product 1

HCID 131736910N-[2-[3-chloro-5-(3,3-dimethyl-1-butynyl)pyridin-2-yl]-2-(isopropoxyimino)ethyl]-2-(trifluoromethyl)benzamideYield 99.7%

Reagents, catalysts & solvents 2

HCID 24350
Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)
Catalyst
HCID 8471TriethylamineSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 0.15 g of N-[2-(5-bromo-3-chloropyridin-2-yl)-2-(isopropoxyimino)ethyl]-2-(trifluoromethyl)benzamide and 0.05 g of 3,3-dimethyl-1-butyne in 3 ml of triethylamine, 0.04 g of copper(I) iodide and 0.02 g of dichlorobistriphenylphosphine palladium(II) were added, and the mixture was stirred at 80° C. for 3 hours. After completion of the reaction, the reaction mixture was allowed to cool to room temperature, mixed with 10 ml of water and extracted with ethyl acetate (20 ml×1). The resulting organic layer was washed with water (10 ml×1) and dried over saturated aqueous sodium chloride and then anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography using ethyl acetate-hexane (with a gradient of from 1:5 to 2:4) as the eluent to obtain 0.15 g of the desired product as a yellow resinous substance.

Workup

  1. customAfter completion of the reaction
  2. temperatureto cool to room temperature
  3. extractionextracted with ethyl acetate (20 ml×1)
  4. washThe resulting organic layer was washed with water (10 ml×1)
  5. dry with materialdried over saturated aqueous sodium chloride
  6. customanhydrous sodium sulfate, and the solvent was evaporated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-18bcfc0220ed4658b8e7553f85be4284
Source dataset
uspto-grants-2016_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09434684B2

Reaction notes

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