Sodium Carbonate → HCID 178440014, compound

HRID 452185Notes

Reaction equation

HRID 452185 reaction equation
I[C:2]1[N:3]=[C:4]([CH2:7][CH2:8][CH3:9])[NH:5][CH:6]=1.[N:10]1[CH:15]=[CH:14][C:13](B(O)O)=[CH:12][CH:11]=1.C(=O)([O-])[O-].[Na+].[Na+]>O1CCOCC1.O>[CH2:7]([C:4]1[NH:5][CH:6]=[C:2]([C:13]2[CH:14]=[CH:15][N:10]=[CH:11][CH:12]=2)[N:3]=1)[CH2:8][CH3:9]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 2734379(Pyridin-4-yl)boronic acidHCID 178440164HCID 178440164, compound

Product 1

HCID 178440014HCID 178440014, compoundYield 37%

Reagents, catalysts & solvents 1

HCID 218864351,4-Dioxane--water (1/1)Solvent

Procedure

[step 1] 4-Iodo-2-propylimidazole obtained in Reference Example A16 was dissolved in dioxane/water (2 mL/1 mL), 4-pyridineboronic acid (0.108 g, 0.889 mmol), 1,1-bisdiphenylphosphinoferrocene dichloropalladium (0.052 g, 0.064 mmol) and sodium carbonate (0.202 g, 1.91 mmol) were added, and the mixture was heated under reflux for 3 hr. The reaction mixture was concentrated under reduced pressure, and the obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate=1/2) to give 2-propyl-4-(4-pyridyl)imidazole (0.044 g, 37%).

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 3 hr
  3. concentrationThe reaction mixture was concentrated under reduced pressure
  4. customthe obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate=1/2)

Sources & evidence

ORD record
ord-cd3ca3096665475ea477baafe384b685
Source dataset
uspto-grants-2013_07
Patent number
US08486980B2

Reaction notes

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