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

HRID 452181
Notes
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Reaction equation

HRID 452181 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:6]=[C:7]([CH3:17])[C:8]2[NH:12][C:11]([CH2:13][CH2:14][CH3:15])=[N:10][C:9]=2[CH:16]=1)=[O:4].CC(C)([O-])C.[K+].Br[CH2:25][C:26]1[CH:43]=[CH:42][C:29]2/[C:30](=[CH:39]/[C:40]#[N:41])/[C:31]3[CH:38]=[CH:37][CH:36]=[CH:35][C:32]=3[CH2:33][CH2:34][C:28]=2[CH:27]=1.C(OCC)(=O)C>CN(C=O)C>[CH3:1][O:2][C:3]([C:5]1[CH:6]=[C:7]([CH3:17])[C:8]2[N:12]=[C:11]([CH2:13][CH2:14][CH3:15])[N:10]([CH2:25][C:26]3[CH:43]=[CH:42][C:29]4/[C:30](=[CH:39]/[C:40]#[N:41])/[C:31]5[CH:38]=[CH:37][CH:36]=[CH:35][C:32]=5[CH2:33][CH2:34][C:28]=4[CH:27]=3)[C:9]=2[CH:16]=1)=[O:4]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 101308354-Methyl-2-propyl-1H-benzimidazole-6-carboxylic acid methyl esterHCID 23665647Potassium tert-butoxideHCID 67210773(E)-(2-bromomethyl-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-ylidene)acetonitrile

Product 1

HCID 67210309(E)-[2-(6-methoxycarbonyl-4-methyl-2-propylbenzimidazol-1-yl)methyl-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-ylidene]acetonitrile
Yield 73%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

[step 1] 6-Methoxycarbonyl-4-methyl-2-propylbenzimidazole (EP502314; 1.19 g, 5.13 mmol) was dissolved in DMF (15 mL), potassium tert-butoxide (0.60 g, 5.3 mmol) was added at 0° C., and the mixture was stirred for 10 min. To this mixture was added a solution of (E)-(2-bromomethyl-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-ylidene)acetonitrile obtained in Reference Example B1 in DMF (8 mL), and the mixture was stirred at room temperature for 2 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 tot/3) to give (E)-[2-(6-methoxycarbonyl-4-methyl-2-propylbenzimidazol-1-yl)methyl-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-ylidene]acetonitrile (1.78 g, 73%).

Workup

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

Sources & evidence

ORD record
ord-bf00c61208d1445ca458d4625ebe651a
Source dataset
uspto-grants-2013_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08486980B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes