Ethyl Acetate → (E)-[2-(6-bromo-4-methyl-2-propylbenzimidazol-1-yl)methyl-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-ylidene]acetonitrile

HRID 452144Notes

Reaction equation

HRID 452144 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH3:14])[C:5]2[NH:9][C:8]([CH2:10][CH2:11][CH3:12])=[N:7][C:6]=2[CH:13]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:22][C:23]1[CH:40]=[CH:39][C:26]2/[C:27](=[CH:36]/[C:37]#[N:38])/[C:28]3[CH:35]=[CH:34][CH:33]=[CH:32][C:29]=3[CH2:30][CH2:31][C:25]=2[CH:24]=1.C(OCC)(=O)C>CN(C=O)C>[Br:1][C:2]1[CH:3]=[C:4]([CH3:14])[C:5]2[N:9]=[C:8]([CH2:10][CH2:11][CH3:12])[N:7]([CH2:22][C:23]3[CH:40]=[CH:39][C:26]4/[C:27](=[CH:36]/[C:37]#[N:38])/[C:28]5[CH:35]=[CH:34][CH:33]=[CH:32][C:29]=5[CH2:30][CH2:31][C:25]=4[CH:24]=3)[C:6]=2[CH:13]=1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 67210773(E)-(2-bromomethyl-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-ylidene)acetonitrileHCID 178439846HCID 178439846, compound

Product 1

HCID 67210768(E)-[2-(6-bromo-4-methyl-2-propylbenzimidazol-1-yl)methyl-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-ylidene]acetonitrileYield 104.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

[step 1] Under a nitrogen atmosphere, 6-bromo-4-methyl-2-propylbenzimidazole (WO2004082621; 300 mg, 1.19 mmol) was dissolved in DMF (3 mL), and the mixture was cooled to 0° C. Potassium carbonate (829 mg, 6.00 mmol) was added, and the mixture was stirred at room temperature for 20 min. To this mixture was added (E)-2-(2-bromomethyl-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-ylidene)acetonitrile (421 mg, 1.30 mmol) obtained in Reference Example B1, and the mixture was stirred at room temperature for 4 hr. Ethyl acetate was added to the mixture, and 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 to 1/3) to give (E)-[2-(6-bromo-4-methyl-2-propylbenzimidazol-1-yl)methyl-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-ylidene]acetonitrile (615 mg, 95%).

Workup

  1. customobtained in Reference Example B1
  2. stirringthe mixture was stirred at room temperature for 4 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 to 1/3)

Sources & evidence

ORD record
ord-0f25278f54a848e49ce1d340ae9eaeee
Source dataset
uspto-grants-2013_07
Patent number
US08486980B2

Reaction notes

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