Potassium Carbonate → HCID 11020512, compound

HRID 2278655Notes

Reaction equation

HRID 2278655 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1B(O)O.C(=O)([O-])[O-].[K+].[K+].Br[C:19]1[CH:27]=[CH:26][CH:25]=[C:24]2[C:20]=1[CH:21]=[CH:22][NH:23]2>O1CCOCC1.O.CC1C=CC=CC=1[P](C1C=CC=CC=1C)([Pd](Cl)(Cl)[P](C1=C(C)C=CC=C1)(C1C=CC=CC=1C)C1C=CC=CC=1C)C1C=CC=CC=1C>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:19]1[CH:27]=[CH:26][CH:25]=[C:24]2[C:20]=1[CH:21]=[CH:22][NH:23]2

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 6764944-BromoindoleHCID 27339582-Methoxyphenylboronic acid

Product 1

HCID 11020512HCID 11020512, compoundYield 49.5%

Reagents, catalysts & solvents 3

HCID 178424406HCID 178424406, compoundCatalystHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

0.73 g of 2-methoxyphenylboronic acid and then 1.66 g of potassium carbonate are successively added to a solution of 0.78 g of 4-bromoindole in 15 ml of dioxane and 5 ml of water under argon. The reaction mixture is stirred at ambient temperature for 15 minutes, and then 0.16 g of dichlorobis(tri-o-tolylphosphine)palladium(II) is added. The reaction mixture is stirred at ambient temperature for 16 hours, and then at 60° C. for 18 hours, and, finally, at 110° C. for 3 hours. After returning to ambient temperature, the mixture is concentrated to dryness under reduced pressure. The residue is taken up in a mixture of 15 ml of a 2N sodium hydroxide solution and 30 ml of ethyl acetate. The mixture is filtered through Clarcel®, and then separated by settling out. The organic phase is separated and the aqueous phase is extracted with 2×30 ml of ethyl acetate. The organic phases are combined, dried over anhydrous magnesium sulfate, filtered, and then concentrated to dryness under reduced pressure. The residue is purified on a 30 g cartridge of 15-40 μm silica, elution being carried out with a 60/40 v/v cyclohexane/dichloromethane mixture, at a flow rate of 30 ml/min. 0.44 g of 4-(2-methoxyphenyl)indole is thus obtained in the form of a pale yellow solid, the characteristics of which are the following:

Workup

  1. stirringThe reaction mixture is stirred at ambient temperature for 16 hours
  2. waitat 60° C. for 18 hours
  3. waitfinally, at 110° C. for 3 hours
  4. customAfter returning to ambient temperature
  5. concentrationthe mixture is concentrated to dryness under reduced pressure
  6. additionThe residue is taken up in a mixture of 15 ml of a 2N sodium hydroxide solution and 30 ml of ethyl acetate
  7. filtrationThe mixture is filtered through Clarcel®
  8. customseparated
  9. customThe organic phase is separated
  10. extractionthe aqueous phase is extracted with 2×30 ml of ethyl acetate
  11. dry with materialdried over anhydrous magnesium sulfate
  12. filtrationfiltered
  13. concentrationconcentrated to dryness under reduced pressure
  14. customThe residue is purified on a 30 g cartridge of 15-40 μm silica, elution

Sources & evidence

ORD record
ord-06af0486d0ab44689b2ffe38c9d5e909
Source dataset
uspto-grants-2015_09
Patent number
US09133168B2

Reaction notes

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