1,10-Phenanthroline → 3-(4-Pyridin-2-yl-imidazol-1-yl)-benzonitrile

Temperature

120 °C

To a flame dried, argon purged screw-cap vial, containing copper (I) triflate.benzene complex (0.01 g, 0.03 mmol), 1,10-phenanthroline (0.10 g, 0.54 mmol), trans-dibenzylideneacetone (0.01 g, 0.03 mmol) and cesium carbonate (0.20g, 0.60 mmol) was added a solution of 4-(2-pyridyl)imidazole (0.08 g, 0.54 mmol) and 3-iodobenzonitrile (0.19 g, 0.82 mmol) in ortho-xylene (2 mL). The resulting brownish black reaction mixture was heated overnight at 120° C. After cooling, the reaction mixture was diluted with dichloromethane (20 mL) and washed sequentially with saturated ammonium chloride (20 mL) and brine (20 mL). The organic phase was then dried with sodium sulfate, filtered, and concentrated in vacuo. Silica gel chromatography of the crude residue using 1% methanol (2 M in ammonia) in dichloromethane afforded 11 mg of 4-(2-pyridyl)-1-(3-cyanophenyl)-1H-imidazole, as an off-white solid.

1. customTo a flame dried
2. customargon purged
3. customscrew-cap vial
4. additioncontaining copper (I) triflate
5. customThe resulting brownish black reaction mixture
6. temperatureAfter cooling
7. washwashed sequentially with saturated ammonium chloride (20 mL) and brine (20 mL)
8. dry with materialThe organic phase was then dried with sodium sulfate
9. filtrationfiltered
10. concentrationconcentrated in vacuo

ORD record

ord-16b5d23edf5a421c90fe9c73a295dcbc

Source dataset

uspto-grants-2003_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06660753B2