Water → 7-Ethenyl-1H-indole

HRID 910069Notes

Reaction equation

HRID 910069 reaction equation
[CH2:1]([Sn](CCCC)(CCCC)C=C)[CH2:2]CC.[Cl-].[Li+].Br[C:19]1[CH:20]=[CH:21][CH:22]=[C:23]2[C:27]=1[NH:26][CH:25]=[CH:24]2.O>CN(C)C=O.C1([Pd-2](Cl)(Cl)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(OCC)(=O)C>[CH:1]([C:19]1[CH:20]=[CH:21][CH:22]=[C:23]2[C:27]=1[NH:26][CH:25]=[CH:24]2)=[CH2:2]

Participants

9

Reactant 4

HCID 962WaterHCID 81998TributylvinyltinHCID 433294Lithium ChlorideHCID 27570207-Bromoindole

Product 1

HCID 145674047-Ethenyl-1H-indoleYield 80%

Reagents, catalysts & solvents 4

HCID 11776TriphenylphosphineCatalystHCID 178479785HCID 178479785, compoundCatalystHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

Add-tributyl(vinyl)tin (9.8 mL, 33.7 mmol), triphenyl-phosphine (0.4 g, 1.53 mmol), diphenylpalladium(II) dichloride (1.07 g, 1.53 mmol) and lithium chloride (4.0 g, 94.4 mmol) to 7-bromo-1H-indole (6.0 g, 30.6 mmol) in 150 mL of dimethylformamide and heat the resulting mixture at 100° C. overnight. Cool the reaction mixture to 20-24° C. and poured into a mixture of 150 mL of water and 150 mL of ethyl acetate. Wash the aqueous layer with additional ethyl acetate (3×100 mL), combine the organic layers, wash with saturated aqueous sodium chloride, dry over magnesium sulfate, filter, and concentrate under reduced pressure. Subject the residue to silica gel chromatography, eluting with 5-10% ethyl acetate in hexanes. Combine fractions containing product and concentrate them under reduced pressure to provide the desired compound as a clear oil (3.5 g, 80%).

Workup

  1. temperatureCool the reaction mixture to 20-24° C.
  2. washWash the aqueous layer with additional ethyl acetate (3×100 mL)
  3. washwash with saturated aqueous sodium chloride
  4. dry with materialdry over magnesium sulfate
  5. filtrationfilter
  6. concentrationconcentrate under reduced pressure
  7. washeluting with 5-10% ethyl acetate in hexanes
  8. additionCombine fractions containing product
  9. concentrationconcentrate them under reduced pressure

Sources & evidence

ORD record
ord-f956cce919854dba9fea3f949893433e
Source dataset
uspto-grants-2011_09
Patent number
US08022065B2

Reaction notes

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