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

HRID 1409501Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1409501
[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. CC (DCM to DCM/EA=3:1 to DCM/MeOH=100:2 to 100:5 to 100:10) gave 3-(4-bromo-2-(diethylcarbamoyl)phenoxy)-2-fluoropyridine 1-oxide as an off white 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

Quellen und Nachweise

ORD-Eintrag
ord-b70e3fb6b6ed474c8dca00d2a685e9be
Quelldatensatz
uspto-grants-2014_12
Patentnummer
US08921363B2

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