Trifluoroacetic acid → 6-(Difluoromethyl)pyridin-3-amine

HRID 217275Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 217275
C(OC(=O)[NH:7][C:8]1[CH:9]=[N:10][C:11]([CH:14]([F:16])[F:15])=[CH:12][CH:13]=1)(C)(C)C.FC(F)(F)C(O)=O.C(=O)([O-])O.[Na+]>ClCCl>[F:15][CH:14]([F:16])[C:11]1[N:10]=[CH:9][C:8]([NH2:7])=[CH:13][CH:12]=1

Komponenten

5

Edukt 3

HCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 57736454HCID 57736454, Verbindung

Produkt 1

HCID 552816746-(Difluoromethyl)pyridin-3-amineAusbeute 60,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A solution of the compound obtained in Step C (5.9 g) in dichloromethane (80 ml) was treated with trifluoroacetic acid (3.7 ml) at ambient temperature for 12 hours. The reaction mixture was poured into aqueous sodium hydrogen carbonate (saturated) and washed several times with dichloromethane. The combined organic layers were washed with brine, dried over sodium sulfate and then concentrated in vacuo. Chromatography on silica gel (eluent: hexane/ethyl acetate 1:1) afforded 6-difluoromethyl-pyridin-3-yl-amine (2.1 g): 1H NMR (400 MHz, CDCl3) 3.98 (br s, 2H), 6.56 (t, 1H), 7.03 (dd, 1H), 7.40 (d, 1H), 8.06 (d, 1H).

Aufarbeitung

  1. washwashed several times with dichloromethane
  2. washThe combined organic layers were washed with brine
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-57a11ef2fb94481b995c21e271858b2a
Quelldatensatz
uspto-grants-2012_06
Patentnummer
US08193362B2

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