Reaktion #2186683

Reaktionsgleichung

2-(4bromo-1H-pyrazol-1-yl)pyridine

3-cyanophenylboronic acid

potassium carbonate

→

3-(1-pyridin-2-yl-1H-pyrazol-4-yl)benzonitrile

Lösungsmittel

ethylene glycol dimethyl ether

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigewas degassed by argon bubbling for 15 min.
2. 2
   Sonstigedegassing
3. 3
   workup.ADDITIONwas added
4. 4
   Extraktionextracted with EtOAc (3×30 mL)
5. 5
   Waschenthe combined extracts washed with brine
6. 6
   TrocknenThe organic phase was dried over Na2SO4
7. 7
   Einengenconcentrated in vacuo
8. 8
   SonstigeThe crude residue was chromatographed on silica gel eluting with EtOAc:hexane (2:3)
9. 9
   Sonstigeto afford a white solid which
10. 10
    Sonstigewas recrystallized from EtOAc/Hexane

Vorschrift

A solution of 2-(4bromo-1H-pyrazol-1-yl)pyridine (0.446 g, 2.0 mmol), 3-cyanophenylboronic acid (0.302 g, 2.0 mmol), potassium carbonate (0.552 g, 4.0 mmol) in a mixture of ethylene glycol dimethyl ether (20 mL) and water (4 mL) was degassed by argon bubbling for 15 min., then tetrakis(triphenylphosphine)palladium(0) (20 mg, 0.017 mmol) was added and degassing continued a further 15 min. The resulting solution was stirred at 70° C. for 14 h, whereupon H2O (30 mL) was added, then extracted with EtOAc (3×30 mL) and the combined extracts washed with brine. The organic phase was dried over Na2SO4 and concentrated in vacuo. The crude residue was chromatographed on silica gel eluting with EtOAc:hexane (2:3) to afford a white solid which was recrystallized from EtOAc/Hexane give 3-(1-pyridin-2-yl-1H-pyrazol-4-yl)benzonitrile as a white solid. MP=160-161° C. 1H NMR (CD3Cl, 300 MHz) δ 8.88 (s, 1H), 8.45 (d, 1H), 8.03 (s, 1H), 8.01 (d, 1H), 7.87 (d, 1H), 7.86 (s, 1H), 7.81 (d, 1H), 7.57˜7.48 (m, 2H), 7.25 (dd, 1H). MS (ESI) 247.1 (M++H).

Quelle