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

HRID 1920273Notes

Reaction equation

HRID 1920273 reaction equation
I[C:2]1[N:6]([CH2:7][CH:8]([CH3:10])[CH3:9])[CH:5]=[N:4][C:3]=1[C:11]#[N:12].O.Cl.[NH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1B(O)O.C(=O)([O-])[O-].[K+].[K+]>COCCOC.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[NH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[C:2]1[N:6]([CH2:7][CH:8]([CH3:10])[CH3:9])[CH:5]=[N:4][C:3]=1[C:11]#[N:12]

Participants

7

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 164270902-Aminophenylboronic acid hydrochlorideHCID 445414195-iodo-1-isobutyl-1H-imidazole-4-carbonitrile

Product 1

HCID 251645955-(2-aminophenyl)-1-(2-methylpropyl)-1H-imidazole-4-carbonitrileYield 100.2%

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
90 °C

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-93088037951647d694a9811072b25b3a
Source dataset
uspto-grants-2012_05
Patent number
US08168802B2

Reaction notes

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