Toluene → {1-[(7-bromo-1H-indol-3-yl)methyl]cyclopropyl}acetonitrile

HRID 12629Notes

Reaction equation

HRID 12629 reaction equation
[C:1]1([CH3:7])[CH:6]=[CH:5]C=[CH:3][CH:2]=1.[Br:8][C:9]1[CH:10]=[CH:11][CH:12]=[C:13]2[C:17]=1[NH:16][CH:15]=[CH:14]2.C([Mg]Br)C.[Cl-].[NH4+:23]>C(OCC)C.C(#N)C>[Br:8][C:9]1[CH:10]=[CH:11][CH:12]=[C:13]2[C:17]=1[NH:16][CH:15]=[C:14]2[CH2:7][C:1]1([CH2:2][C:3]#[N:23])[CH2:6][CH2:5]1

Participants

7

Reactant 4

HCID 1140TolueneHCID 25517Ammonium ChlorideHCID 27570207-BromoindoleHCID 178418443HCID 178418443, compound

Product 1

HCID 68690561{1-[(7-bromo-1H-indol-3-yl)methyl]cyclopropyl}acetonitrile

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6342AcetonitrileSolvent

Procedure

To a toluene (12 mL) solution of 7-bromoindole (1.00 g), [1-bromomethyl)cyclopropyl]acetonitrile (444 mg) was added and a diethyl ether solution (1.7 mL) of 3M ethylmagnesium bromide was added dropwise under ice cooling, and then the mixture was refluxed for 2.5 hours. To the reaction mixture, an aqueous saturated ammonium chloride solution was added under ice cooling, followed by extraction with ethyl acetate. The organic layer was washed with water and saturated saline, dried over anhydrous sodium sulfate and then filtered. The filtrate was concentrated and the residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=90:10 to 80:20) to obtain the titled compound having the following physical properties (390 mg).

Workup

  1. temperaturethe mixture was refluxed for 2.5 hours
  2. extractionfollowed by extraction with ethyl acetate
  3. washThe organic layer was washed with water and saturated saline
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated
  7. customthe residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=90:10 to 80:20)

Sources & evidence

ORD record
ord-bb62d166589e47b08bd5708375452f37
Source dataset
uspto-grants-2010_06
Patent number
US07728023B2

Reaction notes

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