Water → (E)-[2-(2-ethyl-3-methylindol-1-yl)methyl-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-ylidene]acetonitrile

HRID 452141Notes

Reaction equation

HRID 452141 reaction equation
[CH2:1]([C:3]1[NH:4][C:5]2[C:10]([C:11]=1[CH3:12])=[CH:9][CH:8]=[CH:7][CH:6]=2)[CH3:2].[H-].[Na+].Br[CH2:16][C:17]1[CH:34]=[CH:33][C:20]2/[C:21](=[CH:30]/[C:31]#[N:32])/[C:22]3[CH:29]=[CH:28][CH:27]=[CH:26][C:23]=3[CH2:24][CH2:25][C:19]=2[CH:18]=1.O>CN(C=O)C>[CH2:1]([C:3]1[N:4]([CH2:16][C:17]2[CH:34]=[CH:33][C:20]3/[C:21](=[CH:30]/[C:31]#[N:32])/[C:22]4[CH:29]=[CH:28][CH:27]=[CH:26][C:23]=4[CH2:24][CH2:25][C:19]=3[CH:18]=2)[C:5]2[C:10]([C:11]=1[CH3:12])=[CH:9][CH:8]=[CH:7][CH:6]=2)[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 13766362-ethyl-3-methyl-1H-indoleHCID 67210773(E)-(2-bromomethyl-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-ylidene)acetonitrile

Product 1

HCID 67211487(E)-[2-(2-ethyl-3-methylindol-1-yl)methyl-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-ylidene]acetonitrileYield 47.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

[step 1] 2-Ethyl-3-methylindole (196 mg, 1.23 mmol) was dissolved in DMF (3.2 mL), sodium hydride (60%; 49 mg, 1.23 mmol) was added, and the mixture was stirred at room temperature for 15 min. To the reaction mixture was added (E)-2-(2-bromomethyl-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-ylidene)acetonitrile (200 mg, 0.617 mmol) obtained in Reference Example B1, and the mixture was stirred at room temperature for 2 hr. Water was added to the mixture, and the mixture was extracted with ethyl acetate. 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=9/1) to give (E)-[2-(2-ethyl-3-methylindol-1-yl)methyl-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-ylidene]acetonitrile (117 mg, 47%).

Workup

  1. customobtained in Reference Example B1
  2. stirringthe mixture was stirred at room temperature for 2 hr
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe organic layer was washed with brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=9/1)

Sources & evidence

ORD record
ord-ca304c8280684094b237848d058601d2
Source dataset
uspto-grants-2013_07
Patent number
US08486980B2

Reaction notes

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