Ethyl Acetate → (E)-[2-(2-ethyl-5,7-dimethyl-3H-imidazo[4,5-b]pyridin-3-yl)methyl-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-ylidene]acetonitrile

HRID 885437Notes

Reaction equation

HRID 885437 reaction equation
[CH2:1]([C:3]1[NH:13][C:6]2=[N:7][C:8]([CH3:12])=[CH:9][C:10]([CH3:11])=[C:5]2[N:4]=1)[CH3:2].[CH3:14][C:15]([CH3:18])([O-])[CH3:16].[K+].C(O[CH2:24][CH3:25])(=O)C>CN(C=O)C>[CH2:1]([C:3]1[N:13]([CH2:14][C:15]2[CH:18]=[CH:25][C:24]3/[C:14](=[CH:1]/[C:3]#[N:4])/[C:15]4[CH:18]=[CH:6][CH:5]=[CH:10][C:16]=4[CH2:12][CH2:8][C:9]=3[CH:16]=2)[C:6]2=[N:7][C:8]([CH3:12])=[CH:9][C:10]([CH3:11])=[C:5]2[N:4]=1)[CH3:2]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 23665647Potassium tert-butoxideHCID 178437439HCID 178437439, compound

Product 1

HCID 22858094(E)-[2-(2-ethyl-5,7-dimethyl-3H-imidazo[4,5-b]pyridin-3-yl)methyl-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-ylidene]acetonitrileYield 63%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

2-Ethyl-5,7-dimethyl-3H-imidazo[4,5-b]pyridine (0.85 g, 4.8 mmol) was dissolved in DMF (15 mL), and the solution was added with potassium tert-butoxide (0.60 g, 5.3 mmol) at 0° C. followed by stirring for 10 min. Thereto was added a solution of the residue obtained above in DMF (8 mL), and the mixture was stirred at room temperature for 2 hr. Ethyl acetate was added to the mixture, the organic layer was washed with brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=3/1-1/3) to give (E)-[2-(2-ethyl-5,7-dimethyl-3H-imidazo[4,5-b]pyridin-3-yl)methyl-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-ylidene]acetonitrile (1.28 g, 63%).

Workup

  1. additionThereto was added a solution of the residue
  2. stirringthe mixture was stirred at room temperature for 2 hr
  3. washthe organic layer was washed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=3/1-1/3)

Sources & evidence

ORD record
ord-1ea6c3a4fecb4882be07966ee98868f9
Source dataset
uspto-grants-2012_08
Patent number
US08242151B2

Reaction notes

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