Reaktion #2186686

Reaktionsgleichung

2-(1H-Pyrazol-3-yl)pyridine

3-fluorobenzonitrile

K2CO3

H2O

→

3-(3-pyridin-2-yl-1H-pyrazol-1-yl)benzonitrile

Lösungsmittel

DMF

—

( g )

EtOAc

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturAfter cooling to ambient temperature
2. 2
   Sonstigethe EtOAc layer was separated
3. 3
   workup.STIRRINGthe aqueous layer shaken with EtOAc (2×30 mL)
4. 4
   WaschenThe combined organic layers were washed with brine (3×40 mL)
5. 5
   Trocknendried over Na2SO4
6. 6
   Einengenconcentrated onto silica gel
7. 7
   SonstigeThe crude material was purified by liquid chromatography on silica gel eluting with EtOAc:hexane (1:1)
8. 8
   Sonstigeto afford a solid
9. 9
   Sonstigethat was recrystallized from EtOAc-hexane

Vorschrift

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)+

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