Reaktion #48373

ord-f06cba3385d146d3b17067dc2a249813

Reaktionsgleichung

Cl
HCl
[N-]=[N+]=Nc1cc(F)cnc1N
3-azido-5-fluoropyridin-2-amine
O=C([O-])[O-]
Carbonate
Nc1cc(F)cnc1N
title compound
Ausbeute 92.8%
Nc1cc(F)cnc1N
5-Fluoropyridine-2,3-diamine
Ausbeute 92.8%

Lösungsmittel

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    Filtrationthe mixture was filtered
  2. 2
    Waschenrinsed with more tetrahydrofuran
  3. 3
    Einengenconcentrated
  4. 4
    workup.DISSOLUTIONThis residue was dissolved in ethanol (50 mL)
  5. 5
    Sonstigepurged with argon, and 10% palladium on carbon
  6. 6
    workup.ADDITIONwas added (0.15 g)
  7. 7
    workup.ADDITIONHydrogen was introduced (1 atm)
  8. 8
    FiltrationThe catalyst was filtered
  9. 9
    Sonstigethe solvent evaporated from the filtrate

Vorschrift

The HCl salt of 3-azido-5-fluoropyridin-2-amine (1.90 g, 10.0 mmol) was dissolved in tetrahydrofuran (100 mL) and treated with MP-Carbonate (Argonaut, 11.5 g). After 1 h, the mixture was filtered, rinsed with more tetrahydrofuran, and concentrated. This residue was dissolved in ethanol (50 mL), purged with argon, and 10% palladium on carbon was added (0.15 g). Hydrogen was introduced (1 atm) and the reaction stirred until complete. The catalyst was filtered and the solvent evaporated from the filtrate to give the title compound (1.18 g). MS 128.0 (M+1)

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US07745427B2uspto-grants-2010_06