N-bromobutanimide → 5-Bromo-3-(2,6-dichloro-3-fluoro-benzyloxy)-pyridin-2-ylamine

HRID 425911Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 425911
[Cl:1][C:2]1[C:16]([F:17])=[CH:15][CH:14]=[C:13]([Cl:18])[C:3]=1[CH2:4][O:5][C:6]1[C:7]([NH2:12])=[N:8][CH:9]=[CH:10][CH:11]=1.C1C(=O)N([Br:26])C(=O)C1>C(#N)C>[Br:26][C:10]1[CH:11]=[C:6]([O:5][CH2:4][C:3]2[C:13]([Cl:18])=[CH:14][CH:15]=[C:16]([F:17])[C:2]=2[Cl:1])[C:7]([NH2:12])=[N:8][CH:9]=1

Komponenten

4

Edukt 2

HCID 67184N-bromobutanimideHCID 211114003-(2,6-Dichloro-3-fluoro-benzyloxy)-pyridin-2-ylamine

Produkt 1

HCID 211114855-Bromo-3-(2,6-dichloro-3-fluoro-benzyloxy)-pyridin-2-ylamineAusbeute 51 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

5-bromo-3-(2,6-dichloro-3-fluoro-benzyloxy)-pyridin-2-ylamine was prepared following procedure 1. A stirring solution of 3-(2,6-dichloro-3-fluoro-benzyloxy)-pyridin-2-ylamine (9.07 g, 0.03 mol) in acetonitrile was cooled to 0° C. using an ice bath. To this solution was added NBS (5.33 g, 0.03 mol) portionwise. The reaction was stirred at 0° C. for 15 min. The reaction was concentrated to dryness under vacuum. The resulting dark oil was dissolved in EtOAc (500 mL), and purified via silica gel chromatography. The solvents were then removed in vacuo to yield 5-bromo-3-(2,6-dichloro-3-fluoro-benzyloxy)-pyridin-2-ylamine (5.8 g, 0.015 mol, 51%) as a white crystalline solid.

Aufarbeitung

  1. custom5-bromo-3-(2,6-dichloro-3-fluoro-benzyloxy)-pyridin-2-ylamine was prepared
  2. concentrationThe reaction was concentrated to dryness under vacuum
  3. dissolutionThe resulting dark oil was dissolved in EtOAc (500 mL)
  4. custompurified via silica gel chromatography
  5. customThe solvents were then removed in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-e92353001d6d40ff81a529730b262d62
Quelldatensatz
uspto-grants-2012_01
Patentnummer
US08106197B2

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