Pyridine → 6-Bromo-2-(tert-butylcarbonyl)amino-3-methoxypyridine

HRID 1725672Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1725672
[NH2:1][C:2]1[C:7]([O:8][CH3:9])=[CH:6][CH:5]=[C:4]([Br:10])[N:3]=1.N1C=CC=CC=1.[C:17](Cl)(=[O:22])[C:18]([CH3:21])([CH3:20])[CH3:19]>C(Cl)Cl>[Br:10][C:4]1[N:3]=[C:2]([NH:1][C:17]([C:18]([CH3:21])([CH3:20])[CH3:19])=[O:22])[C:7]([O:8][CH3:9])=[CH:6][CH:5]=1

Komponenten

5

Edukt 3

HCID 1049PyridineHCID 62493Pivaloyl chlorideHCID 575629062-Amino-6-bromo-3-methoxypyridine

Produkt 1

HCID 575628846-Bromo-2-(tert-butylcarbonyl)amino-3-methoxypyridine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A dry reaction flask equipped with a nitrogen inlet and magnetic stirring bar was charged with 2-amino-6-bromo-3-methoxypyridine (33) (0.170 g, 0.84 mmol), pyridine (0.126 mL, 1.26 mmol) and CH2Cl2 (5 mL). To this at 0° C. was added pivaloyl chloride (0.113 mL, 0.92 mmol) and then the reaction mixture was stirred at room temperature overnight. The reaction was then quenched with water (25 mL), extracted with CH2Cl2 (2×25 mL), dried over anhydrous sodium sulfate and solvent was removed under reduced pressure to afford 6-bromo-2-(tert-butylcarbonyl)amino-3-methoxypyridine (34). LCMS: purity: 80%; MS (m/z): 287 (MH+).

Aufarbeitung

  1. customA dry reaction flask
  2. customequipped with a nitrogen inlet and magnetic stirring bar
  3. customThe reaction was then quenched with water (25 mL)
  4. extractionextracted with CH2Cl2 (2×25 mL)
  5. dry with materialdried over anhydrous sodium sulfate and solvent
  6. customwas removed under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-28f9038bedd744508277f9bba488830b
Quelldatensatz
uspto-grants-2009_02
Patentnummer
US07491732B2

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