Sodium Carbonate → HCID 178439998, compound

HRID 452184Notes

Reaction equation

HRID 452184 reaction equation
I[C:2]1[N:3]=[C:4]([CH2:7][CH2:8][CH3:9])[NH:5][CH:6]=1.[C:10]1(B(O)O)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.C(=O)([O-])[O-].[Na+].[Na+]>O1CCOCC1.O>[C:10]1([C:2]2[N:3]=[C:4]([CH2:7][CH2:8][CH3:9])[NH:5][CH:6]=2)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 66827Phenylboronic AcidHCID 178440164HCID 178440164, compound

Product 1

HCID 178439998HCID 178439998, compoundYield 77%

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), phenylboronic 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 4-phenyl-2-propylimidazole (0.091 g, 77%).

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-b094c4c827664b12be4107daa14aaf74
Source dataset
uspto-grants-2013_07
Patent number
US08486980B2

Reaction notes

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