Potassium Fluoride → HCID 86660085, compound

HRID 1843061Notes

Reaction equation

HRID 1843061 reaction equation
[F-].[K+].[Cl:3][C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:11]([C:13]2[N:17]([CH3:18])[N:16]=[C:15]([O:19][CH:20]([F:22])[F:21])[C:14]=2I)=[O:12])=[CH:6][C:5]=1[C:24](=[O:31])[NH:25][CH2:26][C:27]([F:30])([F:29])[F:28].[F:32][C:33]([Si](C)(C)C)([F:35])[F:34]>[Cu]I.CN(C)C=O>[Cl:3][C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:11]([C:13]2[N:17]([CH3:18])[N:16]=[C:15]([O:19][CH:20]([F:22])[F:21])[C:14]=2[C:33]([F:35])([F:34])[F:32])=[O:12])=[CH:6][C:5]=1[C:24](=[O:31])[NH:25][CH2:26][C:27]([F:30])([F:29])[F:28]

Participants

6

Reactant 3

HCID 522689Potassium FluorideHCID 552549(Trifluoromethyl)trimethylsilaneHCID 86660086HCID 86660086, compound

Product 1

HCID 86660085HCID 86660085, compoundYield 13.5%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

36.2 mg (0.19 mmol) of copper(I) iodide and 8.8 mg (0.15 mmol) of potassium fluoride are initially introduced in a heat-dried vial under argon, and 4 ml of N,N-dimethylformamide and 70.0 mg (0.12 mmol) of N-{4-chloro-3-[(2,2,2-trifluoroethyl)carbamoyl]phenyl}-3-(difluoromethoxy)-4-iodo-1-methyl-1H-pyrazole-5-carboxamide and 36.0 mg (254 μmol) of trifluoromethyltrimethylsilane are added. The reaction mixture is degassed in the ultrasound, flushed with argon and the closed vial is heated at 80° C. for two hours. The reaction solution is poured onto water and extracted with ethyl acetate. The organic phase is dried over sodium sulphate, filtered and concentrated by evaporation on a rotary evaporator. Chromatographic purification on silica gel gives 8.00 mg of N-{4-chloro-3-[(2,2,2-trifluoroethyl)carbamoyl]phenyl}-3-(difluoromethoxy)-1-methyl-4-(trifluoromethyl)-1H-pyrazole-5-carboxamide (13%).

Workup

  1. additionare added
  2. customThe reaction mixture is degassed in the ultrasound
  3. customflushed with argon
  4. additionThe reaction solution is poured onto water
  5. extractionextracted with ethyl acetate
  6. dry with materialThe organic phase is dried over sodium sulphate
  7. filtrationfiltered
  8. concentrationconcentrated by evaporation on a rotary evaporator
  9. customChromatographic purification on silica gel

Sources & evidence

ORD record
ord-d2e46949614f47818e33330e496a83b0
Source dataset
uspto-grants-2015_02
Patent number
US08946234B2

Reaction notes

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