5-Fluoro-3-pyridinamine → HCID 68157950, Verbindung

HRID 243245

Reaktionsgleichung

Reaktionsgleichung von HRID 243245
[F:1][C:2]1[CH:3]=[C:4]([NH2:8])[CH:5]=[N:6][CH:7]=1.CC(C)([O-])C.[K+].F[C:16]1[C:23]([N+:24]([O-:26])=[O:25])=[CH:22][CH:21]=[C:20]([F:27])[C:17]=1[C:18]#[N:19]>C1COCC1.O>[F:27][C:20]1[C:17]([C:18]#[N:19])=[C:16]([NH:8][C:4]2[CH:5]=[N:6][CH:7]=[C:2]([F:1])[CH:3]=2)[C:23]([N+:24]([O-:26])=[O:25])=[CH:22][CH:21]=1

Komponenten

6

Edukt 3

HCID 5744505-Fluoro-3-pyridinamineHCID 27370302,6-Difluoro-3-nitrobenzonitrileHCID 23665647Potassium tert-butoxide

Produkt 1

HCID 68157950HCID 68157950, VerbindungAusbeute 58 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel2×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a solution of 5-Fluoropyridin-3-ylamine (1.22 g, 10.9 mmol) in THF (30 mL) at −0° C. was added potassium tert-butoxide (2.43 g, 21.7 mmol) and the reaction mixture stirred at 0° C. for 10 min. This solution was added via cannula to a solution of 2,6-difluoro-3-nitrobenzonitrile (2 g, 10.9 mmol) in THF (20 mL) at −78° C. and the dark purple reaction mixture stirred at −78° C. for 10 min. The reaction mixture was diluted with water and extracted with EtOAc (3×30 mL). The combined organic fractions were washed with brine, dried (MgSO4), concentrated in vacuo. The resultant residue was subjected to flash chromatography (SiO2, eluting with 0-100% EtOAc in cyclohexane). The solid obtained was triturated with pentane to give the title compound as an orange solid (1.73 g, 58%). 1H NMR 400 MHz δ (CDCl3): 9.73 (1H, br s), 8.53 (1H, dd, J=9.5, 5.7 Hz), 8.47 (1H, d, J=2.5 Hz), 8.43-8.40 (1H, m), 7.33 (1H, dt, J=8.8, 2.2 Hz), 6.83 (1H, dd, J=9.5, 7.3 Hz).

Aufarbeitung

  1. stirringthe dark purple reaction mixture stirred at −78° C. for 10 min
  2. extractionextracted with EtOAc (3×30 mL)
  3. washThe combined organic fractions were washed with brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated in vacuo
  6. washThe resultant residue was subjected to flash chromatography (SiO2, eluting with 0-100% EtOAc in cyclohexane)
  7. customThe solid obtained
  8. customwas triturated with pentane

Quellen und Nachweise

ORD-Eintrag
ord-ffd45e9668d24a51848844793906f75b
Quelldatensatz
uspto-grants-2014_02
Patentnummer
US08653089B2

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