Indole → HCID 85665091, compound

HRID 128994Notes

Reaction equation

HRID 128994 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.Br[C:11]1[CH:16]=[CH:15][C:14]([CH3:17])=[CH:13][CH:12]=1.[C:18]([O:21][CH2:22]C)(=[O:20])C>N1C=CC=CC=1.[Cu-]=O>[CH3:17][C:14]1[CH:15]=[CH:16][C:11]([N:1]2[C:9]3[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=3)[C:3]([C:18]([O:21][CH3:22])=[O:20])=[CH:2]2)=[CH:12][CH:13]=1

Participants

6

Reactant 3

HCID 798IndoleHCID 78054-BromotolueneHCID 8857Ethyl Acetate

Product 1

HCID 85665091HCID 85665091, compound

Reagents, catalysts & solvents 2

HCID 178419072HCID 178419072, compoundCatalystHCID 1049PyridineSolvent

Procedure

The title A indole (819 mg, 4.67 mmol, 1.0 eq.) and 4-bromotoluene (1.44 ml, 11.69 mmol, 2.5 eq.) were dissolved in pyridine (4.7 ml, 1M) in an argon atmosphere. Copper(I) oxide (668 mg, 4.67 mmol, 1.0 eq.) was added and heated at 130°±5° C. for 8.5 hours. Ethyl acetate was added and the solid was removed by filtration through celite. The filtrate was washed with water (3×40 ml), 0.5N hydrochloric acid (2×50 ml) and saturated sodium hydrogen carbonate solution (40 ml), dried over anhydrous magnesium sulfate and freed of solvent in vacuo. The remaining brown oil was chromatographed on silica gel, eluting with 10% ether in hexane to give the title B compound (1.165 g).

Workup

  1. temperatureheated at 130°±5° C. for 8.5 hours
  2. customthe solid was removed by filtration through celite
  3. washThe filtrate was washed with water (3×40 ml), 0.5N hydrochloric acid (2×50 ml) and saturated sodium hydrogen carbonate solution (40 ml)
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe remaining brown oil was chromatographed on silica gel
  6. washeluting with 10% ether in hexane

Sources & evidence

ORD record
ord-a1bbbfa86b61427598fc9b68ce4b7b43
Source dataset
uspto-grants-1995_11
Patent number
US05466704

Reaction notes

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