2-Amino-5-bromonicotinic acid → 5-Bromo-3-(6,7-difluoro-1,3-benzoxazol-2-yl)pyridin-2-amine

HRID 908420Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 908420
[NH2:1][C:2]1[C:7]([C:8]([OH:10])=O)=[CH:6][C:5]([Br:11])=[CH:4][N:3]=1.[NH2:12][C:13]1[C:18](O)=[C:17]([F:20])[C:16]([F:21])=[CH:15][CH:14]=1>O.[OH-].[Na+].ClCCl>[Br:11][C:5]1[CH:6]=[C:7]([C:8]2[O:10][C:18]3[C:17]([F:20])=[C:16]([F:21])[CH:15]=[CH:14][C:13]=3[N:12]=2)[C:2]([NH2:1])=[N:3][CH:4]=1

Komponenten

6

Edukt 2

HCID 7374452-Amino-5-bromonicotinic acidHCID 27784416-Amino-2,3-difluorophenol

Produkt 1

HCID 673886015-Bromo-3-(6,7-difluoro-1,3-benzoxazol-2-yl)pyridin-2-amineAusbeute 22,5 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittelHCID 14798Sodium HydroxideLösungsmittel

Reaktionsbedingungen

Temperatur
200 °C

Versuchsvorschrift

To a mixture of 2-amino-5-bromo-pyridine-3-carboxylic acid (1 g) and 6-amino-2,3-difluoro-phenol (0.669 g) placed in a round bottom flask was added polyphosphoric acid (10 g). The mixture was heated at 200° C. for 5 hours. A homogenous black mixture was obtained. The mixture was diluted in water and neutralizing to pH 8 with NaOH 2N. The heterogeneous mixture was diluted with dichloromethane. The insoluble was filtered. The organic phase was separated. The aqueous phase was extracted twice with dichloromethane. The combined organic phases were washed with brine, dried on sodium sulfate, evaporated and dried to afford 5-bromo-3-(6,7-difluoro-1,3-benzoxazol-2-yl)pyridin-2-amine (0.338 g). NMR Spectrum: (DMSOd6) 7.54 (ddd, 1H), 7.70 (ddd, 1H), 7.79 (bs, 2H), 8.34 (d, 1H), 8.38 (d, 1H); Mass spectrum: M+H+ 326-328

Aufarbeitung

  1. customplaced in a round bottom flask
  2. customA homogenous black mixture was obtained
  3. filtrationThe insoluble was filtered
  4. customThe organic phase was separated
  5. extractionThe aqueous phase was extracted twice with dichloromethane
  6. washThe combined organic phases were washed with brine
  7. customdried on sodium sulfate
  8. customevaporated
  9. customdried

Quellen und Nachweise

ORD-Eintrag
ord-156fbbb8476e4b2f975d8763b37f2b69
Quelldatensatz
uspto-grants-2011_09
Patentnummer
US08017611B2

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