Dimethylformamide → HCID 58542524, compound

HRID 1843090Notes

Reaction equation

HRID 1843090 reaction equation
[F-].[K+].CN(C)C=O.[CH2:8]([O:10][C:11]([C:13]1[N:17]([CH3:18])[N:16]=[C:15]([CH:19]2[CH2:21][CH2:20]2)[C:14]=1I)=[O:12])[CH3:9].C[Si](C)(C)[C:25]([F:28])([F:27])[F:26]>C(OCC)(=O)C.[Cu]I.O>[CH:19]1([C:15]2[C:14]([C:25]([F:28])([F:27])[F:26])=[C:13]([C:11]([O:10][CH2:8][CH3:9])=[O:12])[N:17]([CH3:18])[N:16]=2)[CH2:21][CH2:20]1

Participants

8

Reactant 4

HCID 6228DimethylformamideHCID 522689Potassium FluorideHCID 552549(Trifluoromethyl)trimethylsilaneHCID 58542506HCID 58542506, compound

Product 1

HCID 58542524HCID 58542524, compoundYield 86.9%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

268 mg (1.40 mmol) of copper(I) iodide and 65.3 mg (1.12 mmol) of potassium fluoride are initially introduced into a heat-dried vial under argon, and 3 ml of N,N-dimethylformamide and 300 mg (0.93 mmol) of ethyl-3-cyclopropyl-4-iodo-1-methyl-1H-pyrazole-5-carboxylate and 0.28 ml (1.87 mmol) of trimethyl(trifluoromethyl)silane are added. The reaction mixture is degassed in the ultrasound, flushed with argon and the closed via is heated at 80° C. for three hours. The cooled reaction solution is admixed with a small amount of water, diluted with ethyl acetate, filtered over silica gel (ethyl acetate) and concentrated by evaporation on a rotary evaporator. Chromatographic purification on silica gel gives 212 mg of ethyl 3-cyclopropyl-1-methyl-4-(trifluoromethyl)-1H-pyrazole-5-carboxylate (86%).

Workup

  1. additionare added
  2. customThe reaction mixture is degassed in the ultrasound
  3. customflushed with argon
  4. customthe closed
  5. customThe cooled reaction solution
  6. filtrationfiltered over silica gel (ethyl acetate)
  7. concentrationconcentrated by evaporation on a rotary evaporator
  8. customChromatographic purification on silica gel

Sources & evidence

ORD record
ord-fbd005f322f94ea4a5f2cd94ca0ce11c
Source dataset
uspto-grants-2015_02
Patent number
US08946234B2

Reaction notes

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