Tert-Butyl nitrite → 4,6-Dibromo-2-(2,4-difluorophenyl)-3-methylpyridine

HRID 394166Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 394166
[Br:1][C:2]1[C:7](N)=[C:6]([Br:9])[C:5]([CH3:10])=[C:4]([C:11]2[CH:16]=[CH:15][C:14]([F:17])=[CH:13][C:12]=2[F:18])[N:3]=1.C(ON=O)(C)(C)C>C1COCC1>[Br:9][C:6]1[CH:7]=[C:2]([Br:1])[N:3]=[C:4]([C:11]2[CH:16]=[CH:15][C:14]([F:17])=[CH:13][C:12]=2[F:18])[C:5]=1[CH3:10]

Komponenten

4

Edukt 2

HCID 10906Tert-Butyl nitriteHCID 226480972,4-Dibromo-6-(2,4-difluorophenyl)-5-methylpyridin-3-amine

Produkt 1

HCID 226480394,6-Dibromo-2-(2,4-difluorophenyl)-3-methylpyridine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

To a stirred solution of 2,4-dibromo-6-(2,4-difluorophenyl)-5-methylpyridin-3-amine (10 g, 26.4 mmol, 1 eq) in THF (100 mL) was added tert-butylnitrite (4.7 mL, 39.6 mmol, 1.5 eq). The solution warmed and gas evolution was evident. After 2 h, the mixture was heated to and maintained at 60° C. for 45 min. The mixture was cooled and concentrated in vacuo. The product was purified by flash column chromatography eluting with 2% Et2O in hexanes to give 4,6-dibromo-2-(2,4-difluorophenyl)-3-methylpyridine. Mass spectrum (ESI) 362.2 (M+1); 364.2 (M+3); 366.2 (M+5).

Aufarbeitung

  1. temperatureThe solution warmed
  2. temperaturethe mixture was heated to and
  3. temperatureThe mixture was cooled
  4. concentrationconcentrated in vacuo
  5. customThe product was purified by flash column chromatography
  6. washeluting with 2% Et2O in hexanes

Quellen und Nachweise

ORD-Eintrag
ord-08df8454c9504f4e9919912e2880ff64
Quelldatensatz
uspto-grants-2004_10
Patentnummer
US06809199B2

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