Potassium Fluoride → HCID 131729033, compound

HRID 1013423Notes

Reaction equation

HRID 1013423 reaction equation
[F-].[K+].[C:3]([O:7][C:8]([N:10]1[CH2:17][CH:16]2[CH:12]([CH2:13][C:14]3[C:20]([Br:21])=[C:19](I)[S:18][C:15]=32)[CH2:11]1)=[O:9])([CH3:6])([CH3:5])[CH3:4].[F:23][C:24]([Si](C)(C)C)([F:26])[F:25]>CN(C=O)C.CN1CCCC1=O.[Cu]I>[C:3]([O:7][C:8]([N:10]1[CH2:17][CH:16]2[CH:12]([CH2:13][C:14]3[C:20]([Br:21])=[C:19]([C:24]([F:26])([F:25])[F:23])[S:18][C:15]=32)[CH2:11]1)=[O:9])([CH3:6])([CH3:5])[CH3:4]

Participants

6

Reactant 3

HCID 522689Potassium FluorideHCID 552549(Trifluoromethyl)trimethylsilaneHCID 131729034HCID 131729034, compound

Product 1

HCID 131729033HCID 131729033, compound

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 22708839N,N-dimethylformamide 1-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
80 °C

Procedure

Dipyridyl (31 mg, 0.20 mmol), CuI (34 mg, 0.18 mmol) and KF (10 mg, 0.18 mmol) were added to a solution of the product from step b) (78 mg, 0.17 mmol) in 1.6 mL of 1:1 DMF/1-methyl-2-pyrollidinone. The reaction mixture was stirred for 1 hour at 80° C. and then cooled to room temperature. Next, trifluoromethyl trimethylsilane (118 mg, 0.83 mmol) was added and the reaction mixture was heated to 80° C. for 12 hours. The reaction was cooled to room temperature and filtered through a silica plug eluting with CH2Cl2 (10 ml). The organic mixture was washed with brine (2×3 mL), dried with MgSO4, and was concentrated to a dark oil that was purified by preparative LC/MS to give the subtitle compound. MS calculated for C15H17BrF3NO2S +H: 412, observed: 413.

Workup

  1. temperaturecooled to room temperature
  2. temperaturethe reaction mixture was heated to 80° C. for 12 hours
  3. temperatureThe reaction was cooled to room temperature
  4. filtrationfiltered through a silica plug
  5. washeluting with CH2Cl2 (10 ml)
  6. washThe organic mixture was washed with brine (2×3 mL)
  7. dry with materialdried with MgSO4
  8. concentrationwas concentrated to a dark oil that
  9. customwas purified by preparative LC/MS

Sources & evidence

ORD record
ord-3fff9de4f71146b5a6efa778fd9c5a08
Source dataset
uspto-grants-2011_07
Patent number
US07981919B2

Reaction notes

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