Phosphorus oxychloride → N-(5-bromo-2-pyridinyl)-(2-nitro)-5fluorophenylcarboxamide

HRID 12138

Reaktionsgleichung

Reaktionsgleichung von HRID 12138
[F:1][C:2]1[CH:3]=[CH:4][C:5]([N+:11]([O-:13])=[O:12])=[C:6]([CH:10]=1)[C:7]([OH:9])=O.[NH2:14][C:15]1[CH:20]=[CH:19][C:18]([Br:21])=[CH:17][N:16]=1.P(Cl)(Cl)(Cl)=O>N1C=CC=CC=1>[Br:21][C:18]1[CH:19]=[CH:20][C:15]([NH:14][C:7]([C:6]2[CH:10]=[C:2]([F:1])[CH:3]=[CH:4][C:5]=2[N+:11]([O-:13])=[O:12])=[O:9])=[N:16][CH:17]=1

Komponenten

5

Edukt 3

HCID 24813Phosphorus oxychlorideHCID 706222-Amino-5-bromopyridineHCID 27374205-Fluoro-2-nitrobenzoic acid

Produkt 1

HCID 22596298N-(5-bromo-2-pyridinyl)-(2-nitro)-5fluorophenylcarboxamideAusbeute 68,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel

Versuchsvorschrift

A solution of 5-fluoro-2-nitrobenzoic acid (10.0 g, 54 mmol, 1.0 equiv), 2-amino-5-bromopyridine (12.2 g, 1.3 equiv), in 80 mL of pyridine was treated with phosphorous oxychloride (25.3 g, 3.0 equiv) for 30 min. The volatile was evaporated and the residue was redissolved into EtOAc, washed with 1N HCl, saturated aqueous NaHCO3 and saturated aqueous NaCl. The organic layer was dried over Na2SO4, filtered, and evaporated. The volatile was evaporated, and the product was triturated with diethyl ether to give N-(5-bromo-2-pyridinyl)-(2-nitro)-5-fluorophenylcarboxamide (12.5 g, 68%). MS found for C12H7BrFN3O3 (M+H)+: 340, 342.

Aufarbeitung

  1. customThe volatile was evaporated
  2. dissolutionthe residue was redissolved into EtOAc
  3. washwashed with 1N HCl, saturated aqueous NaHCO3 and saturated aqueous NaCl
  4. dry with materialThe organic layer was dried over Na2SO4
  5. filtrationfiltered
  6. customevaporated
  7. customThe volatile was evaporated
  8. customthe product was triturated with diethyl ether

Quellen und Nachweise

ORD-Eintrag
ord-b7fdc228ba5a4a11b5ad77c59bddf049
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07727982B2

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