Trifluoroacetic acid → Methyl 6-amino-4-bromopyridine-2-carboxylate

HRID 1725482Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1725482
[Br:1][C:2]1[CH:7]=[C:6]([NH:8]C(OC(C)(C)C)=O)[N:5]=[C:4]([C:16]([O:18][CH3:19])=[O:17])[CH:3]=1.FC(F)(F)C(O)=O>C(Cl)(Cl)Cl>[NH2:8][C:6]1[N:5]=[C:4]([C:16]([O:18][CH3:19])=[O:17])[CH:3]=[C:2]([Br:1])[CH:7]=1

Komponenten

4

Edukt 2

HCID 6422Trifluoroacetic acidHCID 25067269Methyl 4-bromo-6-[(tert-butoxycarbonyl)amino]pyridine-2-carboxylate

Produkt 1

HCID 29919299Methyl 6-amino-4-bromopyridine-2-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6212ChloroformLösungsmittel

Versuchsvorschrift

7.23 g of methyl 4-bromo-6-t-butoxycarbonylamino-pyridine-2-carboxylate was dissolved in 30 ml of chloroform, and then 15 ml of trifluoroacetic acid was added thereto, followed by stirring at room temperature for 1 hour. After concentrating the reaction mixture, the residue was dissolved in ethyl acetate and washed with saturated sodium bicarbonate and brine. The organic layer was dried over anhydrous magnesium sulfate, filtered, and then concentrated in vacuo. The residue was purified by a silica gel column chromatography (eluent: chloroform to chloroform/methanol=20/1) to give the title compound.

Aufarbeitung

  1. concentrationAfter concentrating the reaction mixture
  2. dissolutionthe residue was dissolved in ethyl acetate
  3. washwashed with saturated sodium bicarbonate and brine
  4. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by a silica gel column chromatography (eluent: chloroform to chloroform/methanol=20/1)

Quellen und Nachweise

ORD-Eintrag
ord-91e3626e3eda4642a651e40e6562093a
Quelldatensatz
uspto-grants-2009_02
Patentnummer
US07491720B2

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