Water → 5-(2-aminophenyl)-1-(2-methylpropyl)-1H-imidazole-4-carbonitrile

Temperatur

90 °C

A solution of 5-iodo-1-(2-methylpropyl)-1H-imidazole-4-carbonitrile (0.15 g, 0.54 mmol) in 1,2-dimethoxyethane (DME) (6 mL) and then water (3 mL) were added to a mixture of 2-aminophenylboronic acid hydrochloride (0.21 g, 1.2 mmol) and potassium carbonate (0.27 g, 1.9 mmol), and the mixture was evacuated and purged with nitrogen three times. Dichlorobis(triphenylphosphine)palladium(II) (16 mg, 0.02 mmol) was added, and the mixture was flushed with nitrogen and heated at reflux (90° C.) for one hour and allowed to cool to room temperature. The reaction mixture was filtered through a layer of CELITE filter aid, and the filter cake was washed with water (30 mL) and dichloromethane (40 mL). The filtrate layers were separated, and the aqueous layer was extracted with dichloromethane (20 mL). The combined organic fractions were concentrated under reduced pressure, and the residue was purified by column chromatography on silica gel to provide 0.13 g of 5-(2-aminophenyl)-1-(2-methylpropyl)-1H-imidazole-4-carbonitrile as an amber liquid that crystallized upon standing for 20 minutes.

1. customthe mixture was evacuated
2. custompurged with nitrogen three times
3. customthe mixture was flushed with nitrogen
4. temperatureheated
5. temperatureto cool to room temperature
6. filtrationThe reaction mixture was filtered through a layer of CELITE
7. filtrationfilter aid
8. washthe filter cake was washed with water (30 mL) and dichloromethane (40 mL)
9. customThe filtrate layers were separated
10. extractionthe aqueous layer was extracted with dichloromethane (20 mL)
11. concentrationThe combined organic fractions were concentrated under reduced pressure
12. customthe residue was purified by column chromatography on silica gel

ORD-Eintrag

ord-93088037951647d694a9811072b25b3a

Quelldatensatz

uspto-grants-2012_05

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08168802B2