Sodium Hydroxide → 5-Bromo-3-(7-fluoro-1,3-benzoxazol-2-yl)pyridin-2-amine

HRID 908422Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 908422
[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[CH:18]=[CH:17][CH:16]=[C:15]([F:19])[C:14]=1O.[OH-].[Na+]>O>[Br:11][C:5]1[CH:6]=[C:7]([C:8]2[O:10][C:14]3[C:15]([F:19])=[CH:16][CH:17]=[CH:18][C:13]=3[N:12]=2)[C:2]([NH2:1])=[N:3][CH:4]=1

Komponenten

5

Edukt 3

HCID 14798Sodium HydroxideHCID 6435622-Amino-6-fluorophenolHCID 7374452-Amino-5-bromonicotinic acid

Produkt 1

HCID 673882065-Bromo-3-(7-fluoro-1,3-benzoxazol-2-yl)pyridin-2-amineAusbeute 33,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
200 °C

Versuchsvorschrift

A mixture of 2-amino-5-bromo-pyridine-3-carboxylic acid (1 g), 2-amino-6-fluoro-phenol (0.586 g) and polyphosphoric acid (10 g) was stirred at 200° C. for 5 hours. The resulting mixture was cooled to room temperature, diluted with water (4 ml) and basified to pH 12 with aqueous NaOH 10N, then 2N. The precipitate was filtered, washed with water, diethyl ether, and dried. The compound was stirred in THF during 2 days, the insoluble was filtered, the filtrate was concentrated to dryness and dried under vacuum to give 5-bromo-3-(7-fluoro-1,3-benzoxazol-2-yl)pyridin-2-amine (0.475 g). NMR Spectrum: (DMSOd6) 7.37-7.48 (m, 2H), 7.69 (dd, 1H), 7.83 (bs, 2H), 8.34 (d, 1H), 8.38 (d, 1H); Mass spectrum: M+H+ 307-309

Aufarbeitung

  1. temperatureThe resulting mixture was cooled to room temperature
  2. filtrationThe precipitate was filtered
  3. washwashed with water, diethyl ether
  4. customdried
  5. stirringThe compound was stirred in THF during 2 days
  6. filtrationthe insoluble was filtered
  7. concentrationthe filtrate was concentrated to dryness
  8. customdried under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-bd152d22d4b94240b557e3579104edb6
Quelldatensatz
uspto-grants-2011_09
Patentnummer
US08017611B2

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