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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
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 452181
[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]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 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

Produkt 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
Ausbeute 73 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel2×

Versuchsvorschrift

[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%).

Aufarbeitung

  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)

Quellen und Nachweise

ORD-Eintrag
ord-bf00c61208d1445ca458d4625ebe651a
Quelldatensatz
uspto-grants-2013_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08486980B2

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