Water → 3-(3-Pyridin-2-yl-pyrazol-1-yl)-benzonitrile

HRID 2099504

Reaktionsgleichung

Reaktionsgleichung von HRID 2099504
[NH:1]1[CH:5]=[CH:4][C:3]([C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][N:7]=2)=[N:2]1.F[C:13]1[CH:14]=[C:15]([CH:18]=[CH:19][CH:20]=1)[C:16]#[N:17].C([O-])([O-])=O.[K+].[K+].O>CN(C=O)C.CCOC(C)=O>[N:7]1[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=1[C:3]1[CH:4]=[CH:5][N:1]([C:13]2[CH:14]=[C:15]([CH:18]=[CH:19][CH:20]=2)[C:16]#[N:17])[N:2]=1

Komponenten

7

Edukt 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 678803-FluorobenzonitrileHCID 27976572-(1H-Pyrazol-3-Yl)Pyridine

Produkt 1

HCID 101927683-(3-Pyridin-2-yl-pyrazol-1-yl)-benzonitrile

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
145 °C

Versuchsvorschrift

2-(1H-Pyrazol-3-yl)pyridine (435 mg, 3 mmol), 3-fluorobenzonitrile (0.32 mL, 3 mmol) and K2CO3 (830 mg, 6 mmol) were dissolved in DMF (10 mL) under Ar (g) and heated at 145° C. for 18 h. After cooling to ambient temperature, H2O (40 mL) and EtOAc (40 mL) were added and the reaction mixture shaken, the EtOAc layer was separated and the aqueous layer shaken with EtOAc (2×30 mL). The combined organic layers were washed with brine (3×40 mL), dried over Na2SO4 and concentrated onto silica gel. The crude material was purified by liquid chromatography on silica gel eluting with EtOAc:hexane (1:1) to afford a solid that was recrystallized from EtOAc-hexane to give 3-(3-pyridin-2-yl-1H-pyrazol-1-yl)benzonitrile as a solid. 1H NMR (CD3Cl, 300 MHz) δ 8.68-8.71 (1H, m), 8.18 (1H, m), 8.12-8.15 (1H, m), 8.02-8.06 (2H, m), 7.81 (1H, ddd), 7.60-7.62 (2H, m), 7.30 (1H, ddd), 7.20 (1H, d). MS (ESI) 247 (M+H)+

Aufarbeitung

  1. temperatureAfter cooling to ambient temperature
  2. customthe EtOAc layer was separated
  3. stirringthe aqueous layer shaken with EtOAc (2×30 mL)
  4. washThe combined organic layers were washed with brine (3×40 mL)
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated onto silica gel
  7. customThe crude material was purified by liquid chromatography on silica gel eluting with EtOAc:hexane (1:1)
  8. customto afford a solid
  9. customthat was recrystallized from EtOAc-hexane

Quellen und Nachweise

ORD-Eintrag
ord-388019c2f29841dab091fc013b25a4f2
Quelldatensatz
uspto-grants-2009_08
Patentnummer
US07569592B2

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