1-Propanol → 5-(2-aminophenyl)-1,2-dimethyl-1H-imidazole-4-carbonitrile

HRID 1920254Notes

Reaction equation

HRID 1920254 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1B(O)O.Br[C:12]1[N:16]([CH3:17])[C:15]([CH3:18])=[N:14][C:13]=1[C:19]#[N:20].C(O)CC.C(=O)([O-])[O-].[Na+].[Na+]>C1(C)C=CC=CC=1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O>[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:12]1[N:16]([CH3:17])[C:15]([CH3:18])=[N:14][C:13]=1[C:19]#[N:20]

Participants

9

Reactant 4

HCID 10311-PropanolHCID 10340Sodium CarbonateHCID 2773216(2-Aminophenyl)boronic acidHCID 23583878960254-14-2

Product 1

HCID 585001475-(2-aminophenyl)-1,2-dimethyl-1H-imidazole-4-carbonitrileYield 98.9%

Reagents, catalysts & solvents 4

HCID 11776TriphenylphosphineCatalystHCID 167845palladium(II) acetateCatalystHCID 962WaterSolventHCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

2-Aminophenylboronic acid (238 mg, 1.74 mmol), 5-bromo-1,2-dimethyl-1H-imidazole-4-carbonitrile (0.200 g, 1.00 mmol), and n-propanol (1.75 mL) were combined and placed under a nitrogen atmosphere. Palladium (II) acetate (134 μL of a 5 mg/mL solution in toluene, 0.003 mmol), triphenylphosphine (2.4 mg, 0.009 mmol), aqueous sodium carbonate (0.600 mL of 2 M) and water (0.350 mL) were added, and the vessel was evacuated and filled with nitrogen three times. The reaction was sealed and heated under a nitrogen atmosphere at 100° C. for four hours, allowed to cool to room temperature, further cooled with ice, and then partitioned between 2M aqueous sodium carbonate and dichloromethane. The aqueous layer was separated and extracted twice with chloroform. The combined organic fractions were dried over magnesium sulfate, filtered, and concentrated under reduced pressure to provide 210 mg of 5-(2-aminophenyl)-1,2-dimethyl-1H-imidazole-4-carbonitrile as a brown oil that crystallized upon standing.

Workup

  1. customthe vessel was evacuated
  2. additionfilled with nitrogen three times
  3. customThe reaction was sealed
  4. temperatureto cool to room temperature
  5. temperaturefurther cooled with ice
  6. custompartitioned between 2M aqueous sodium carbonate and dichloromethane
  7. customThe aqueous layer was separated
  8. extractionextracted twice with chloroform
  9. dry with materialThe combined organic fractions were dried over magnesium sulfate
  10. filtrationfiltered
  11. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-5d11b3780c214856951e56fd649e1160
Source dataset
uspto-grants-2012_05
Patent number
US08168802B2

Reaction notes

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