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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
ノート
印刷プレビュー

反応式

HRID 452181 の反応式
[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]
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 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

生成物 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
収率 73%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒2 回

実験手順

[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%).

後処理

  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)

出典と根拠

ORDレコード
ord-bf00c61208d1445ca458d4625ebe651a
出典データセット
uspto-grants-2013_07
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08486980B2

反応ノート

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