Methyl 2-amino-5-fluoro-3-hydroxybenzoate → Methyl 2-amino-6-fluorobenzoxazole-4-carboxylate

HRID 249913

Reaktionsgleichung

Reaktionsgleichung von HRID 249913
[N:1]1(C(N2C=CN=C2)N)C=CN=[CH:2]1.[CH3:13][O:14][C:15](=[O:25])[C:16]1[CH:21]=[C:20]([F:22])[CH:19]=[C:18]([OH:23])[C:17]=1[NH2:24]>C1COCC1>[NH2:1][C:2]1[O:23][C:18]2[C:17](=[C:16]([C:15]([O:14][CH3:13])=[O:25])[CH:21]=[C:20]([F:22])[CH:19]=2)[N:24]=1

Komponenten

4

Edukt 2

HCID 66873693Methyl 2-amino-5-fluoro-3-hydroxybenzoateHCID 66874404di(1H-imidazole-1-yl)methanamine

Produkt 1

HCID 66873549Methyl 2-amino-6-fluorobenzoxazole-4-carboxylateAusbeute 87 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of di(1H-imidazole-1-yl)methanamine (1.05 g, 6.52 mmol) in THF (30 mL) was added methyl-2-amino-5-fluoro-3-hydroxybenzoate (0.96 g, 5.22 mmol) at room temperature and the resulting reaction mixture was heated to reflux for 6 h. The reaction mixture was cooled to room temperature and concentrated under reduced pressure. The residue was dissolved in EtOAc (200 mL) and washed with H2O (4×100 mL), saturated aqueous ammonium chloride (2×100 mL), brine (2×100 mL), dried over Na2SO4, filtered, and concentrated under reduced pressure to afford methyl 2-amino-6-fluorobenzoxazole-4-carboxylate (0.95 g, 87%). 1H NMR and MS consistent.

Aufarbeitung

  1. customthe resulting reaction mixture
  2. temperaturewas heated
  3. temperatureto reflux for 6 h
  4. concentrationconcentrated under reduced pressure
  5. dissolutionThe residue was dissolved in EtOAc (200 mL)
  6. washwashed with H2O (4×100 mL), saturated aqueous ammonium chloride (2×100 mL), brine (2×100 mL)
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-6d1d6fce54a148068c48605bb82d70fd
Quelldatensatz
uspto-grants-2011_01
Patentnummer
US07863271B2

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