Trifluoroacetic acid → 2-Chloro-3-fluoropyridin-4-amine

HRID 2366205Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2366205
C(O)(C(F)(F)F)=O.C(OC(=O)[NH:14][C:15]1[CH:20]=[CH:19][N:18]=[C:17]([Cl:21])[C:16]=1[F:22])(C)(C)C>C(Cl)Cl>[Cl:21][C:17]1[C:16]([F:22])=[C:15]([NH2:14])[CH:20]=[CH:19][N:18]=1

Komponenten

4

Edukt 2

HCID 6422Trifluoroacetic acidHCID 86723306Tert-butyl (2-chloro-3-fluoropyridin-4-yl)carbamate

Produkt 1

HCID 601502892-Chloro-3-fluoropyridin-4-amineAusbeute 94 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

TFA (5 mL) was added to a solution of (2-chloro-3-fluoropyridin-4-yl)carbamic acid tert-butyl ester (1.9 g, 7.7 mmol) in DCM (10 mL). The solution was stirred at ambient temperature for 5 hours and concentrated under reduced pressure. The resultant residue was dissolved in DCM and purified by column chromatography on a NH2 cartridge (0-10% MeOH in DCM) to afford the title compound as a beige solid (0.96 g, 94% yield). 1H NMR (400 MHz, CDCl3): δ 7.82 (d, J=5.4 Hz, 1H), 6.60 (t, J=5.8 Hz, 1H), 4.38 (br s, 2H).

Aufarbeitung

  1. concentrationconcentrated under reduced pressure
  2. dissolutionThe resultant residue was dissolved in DCM
  3. custompurified by column chromatography on a NH2 cartridge (0-10% MeOH in DCM)

Quellen und Nachweise

ORD-Eintrag
ord-ba6feace598d4ca48f72404c67666cc4
Quelldatensatz
uspto-grants-2014_04
Patentnummer
US08697708B2

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