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

HRID 1855293Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1855293
[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

Komponenten

5

Edukt 3

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-d7d899e26d924028ba267d642bd4dca1
Quelldatensatz
uspto-grants-2015_02
Patentnummer
US08962859B2

Notizen zur Reaktion

Wird geladen…