Potassium Carbonate → HCID 59317814, compound

HRID 2067698Notes

Reaction equation

HRID 2067698 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[CH:5]2.C(=O)([O-])[O-].[K+].[K+].I[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>[Cu]Br>[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[CH:6]=[CH:5]2

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 11575IodobenzeneHCID 249055-Bromoindole

Product 1

HCID 59317814HCID 59317814, compoundYield 33.1%

Reagents, catalysts & solvents 1

HCID 24593copper(I) bromideCatalyst

Conditions

Temperature
100 °C

Procedure

A mixture of 5-bromoindole (10 g), potassium carbonate (27 g), copper (I) bromide (0.73 g) and iodobenzene (135 g) was heated to 100° C., then was removed once from the oil bath, sodium hydroxide (1.58 g) and copper (II) acetate (50 mg) were added and the mixture was stirred at 140° C. for 9 hours. From the reaction solution, the insolubles were filtered off, the filtrate was distilled off in vacuo, and the residue obtained was purified by silica gel column chromatography (hexane:ethyl acetate=19:1 to 3:2) to afford the above-identified compound (4.6 g).

Workup

  1. customwas removed once from the oil bath, sodium hydroxide (1.58 g) and copper (II) acetate (50 mg)
  2. additionwere added
  3. filtrationFrom the reaction solution, the insolubles were filtered off
  4. distillationthe filtrate was distilled off in vacuo
  5. customthe residue obtained
  6. customwas purified by silica gel column chromatography (hexane:ethyl acetate=19:1 to 3:2)

Sources & evidence

ORD record
ord-3335e72bd41b480fa66214a1e5de3bb0
Source dataset
uspto-grants-2012_10
Patent number
US08293781B2

Reaction notes

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