Ethyl Acetate → 6-(4-methoxyphenyl)-1H-indole

HRID 2192241Notes

Reaction equation

HRID 2192241 reaction equation
Br[C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[CH:7][NH:8]2)=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[CH3:17][O:18][C:19]1[CH:24]=[CH:23][C:22](B(O)O)=[CH:21][CH:20]=1.C(OCC)(=O)C>CN(C=O)C.O.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].O>[CH3:17][O:18][C:19]1[CH:24]=[CH:23][C:22]([C:2]2[CH:10]=[C:9]3[C:5]([CH:6]=[CH:7][NH:8]3)=[CH:4][CH:3]=2)=[CH:21][CH:20]=1

Participants

8

Reactant 4

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 201262(4-Methoxyphenyl)boronic acidHCID 6764936-Bromoindole

Product 1

HCID 152927466-(4-methoxyphenyl)-1H-indole

Reagents, catalysts & solvents 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 962WaterSolventHCID 21962138N,N-Dimethylformamide--water (1/1)Solvent

Procedure

6-Bromo-1H-indole (1.00 g, 5.10 mmol) and potassium carbonate (1.41 g, 10.2 mmol) were dissolved in a mixture solution of DMF/water (4:1, 10.0 mL), and the gas included in the mixture solution was removed using ultrasonic waves and nitrogen gas. After sequentially adding 4-methoxyphenylboronic acid (853 mg, 5.61 mmol) and Pd(dppf)Cl2 (416 mg, 0.51 mmol), the mixture was stirred at room temperature in a sealed state. 2 hours later, ethyl acetate and water were added and the reaction solution was filtered using a diatomite pad. After separation of the organic layer, the aqueous layer was extracted with ethyl acetate. The collected organic layer was concentrated by drying with anhydrous magnesium sulfate. The residue was purified by chromatography (silica gel, EA:Hx=1:4). The target compound was obtained as white solid.

Workup

  1. customwas removed
  2. filtrationthe reaction solution was filtered
  3. customAfter separation of the organic layer
  4. extractionthe aqueous layer was extracted with ethyl acetate
  5. concentrationThe collected organic layer was concentrated
  6. dry with materialby drying with anhydrous magnesium sulfate
  7. customThe residue was purified by chromatography (silica gel, EA:Hx=1:4)
  8. customThe target compound was obtained as white solid

Sources & evidence

ORD record
ord-1414cb4afe9d4ec18ca6f9becb062465
Source dataset
uspto-grants-2012_12
Patent number
US08329708B2

Reaction notes

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