Trifluoroacetic anhydride → 3-(4-Bromo-2-(diethylcarbamoyl)phenoxy)-2-fluoropyridine 1-oxide

HRID 1855293Notes

Reaction equation

HRID 1855293 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:15][C:16]2[C:17]([F:22])=[N:18][CH:19]=[CH:20][CH:21]=2)=[C:6]([CH:14]=1)[C:7]([N:9]([CH2:12][CH3:13])[CH2:10][CH3:11])=[O:8].C(N)(N)=[O:24].OO.FC(F)(F)C(OC(=O)C(F)(F)F)=O>C(Cl)Cl>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:15][C:16]2[C:17]([F:22])=[N+:18]([O-:24])[CH:19]=[CH:20][CH:21]=2)=[C:6]([C:7](=[O:8])[N:9]([CH2:12][CH3:13])[CH2:10][CH3:11])[CH:14]=1

Participants

5

Reactant 3

HCID 9845Trifluoroacetic anhydrideHCID 31294Carbamide PeroxideHCID 667282945-bromo-N,N-diethyl-2-(2-fluoropyridin-3-yloxy)benzamide

Product 1

HCID 667281373-(4-Bromo-2-(diethylcarbamoyl)phenoxy)-2-fluoropyridine 1-oxide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 5-bromo-N,N-diethyl-2-(2-fluoropyridin-3-yloxy)benzamide (1.4 g, 3.81 mmol) and urea peroxide (1.076 g, 11.44 mmol) in 10 mL of DCM at 0 C was added dropwise trifluoroacetic anhydride (1.601 mL, 11.44 mmol) and the resulting reaction was stirred overnight. LCMS showed only less than 50% of desired conversion. The mixture was evaporated to dryness, quenched with Sat. NaHCO3, extracted with EA, dried over Na2SO4, filtered and evaporated to dryness. The crude product was purified using column chromatography (DCM to DCM/EA=3:1 to DCM/MeOH=100:2 to 100:5 to 100:10) to provide 3-(4-bromo-2-(diethylcarbamoyl)phenoxy)-2-fluoropyridine 1-oxide as an offwhite solid.

Workup

  1. customthe resulting reaction
  2. customThe mixture was evaporated to dryness
  3. customquenched with Sat. NaHCO3
  4. extractionextracted with EA
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. customevaporated to dryness
  8. customThe crude product was purified

Sources & evidence

ORD record
ord-d7d899e26d924028ba267d642bd4dca1
Source dataset
uspto-grants-2015_02
Patent number
US08962859B2

Reaction notes

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