Potassium Carbonate → 6-bromo-1-(4-ethoxyphenyl)-1H-indole

HRID 1948683

Reaktionsgleichung

Reaktionsgleichung von HRID 1948683
[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[CH:7][NH:8]2)=[CH:4][CH:3]=1.I[C:12]1[CH:17]=[CH:16][C:15]([O:18][CH2:19][CH3:20])=[CH:14][CH:13]=1.C(=O)([O-])[O-].[K+].[K+].N1CCC[C@H]1C(O)=O>CS(C)=O.[Cu]I.O>[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[CH:7][N:8]2[C:12]2[CH:17]=[CH:16][C:15]([O:18][CH2:19][CH3:20])=[CH:14][CH:13]=2)=[CH:4][CH:3]=1

Komponenten

8

Edukt 4

HCID 11430Potassium CarbonateHCID 145742L-ProlineHCID 2207001-Ethoxy-4-iodobenzeneHCID 6764936-Bromoindole

Produkt 1

HCID 669202456-bromo-1-(4-ethoxyphenyl)-1H-indoleAusbeute 56,4 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)KatalysatorHCID 679Dimethyl SulfoxideLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

A solution of 1.0 g (5 mmol) of 6-bromo-1H-indole, 1.06 g (4.15 mmol) of 4-iodophenetole, 1.45 g of potassium carbonate, 38.1 mg of copper(I) iodide and 42 mg of L-proline in 15 ml of dimethyl sulfoxide is heated at 120° C. for 15 hours. The reaction mixture is then cooled to room temperature, 30 ml of water are added, and the mixture is extracted three times with 20 ml of ethyl acetate each time. After the combined organic phases have been dried over sodium sulfate, the solvent is stripped off in a rotary evaporator, and the crude product is purified by column chromatography on silica gel (n-heptane/ethyl acetate 98:2), giving 0.74 g of 6-bromo-1-(4-ethoxyphenyl)-1H-indole as brownish resin; LC/MS: 317 (M+H).

Aufarbeitung

  1. extractionthe mixture is extracted three times with 20 ml of ethyl acetate each time
  2. dry with materialAfter the combined organic phases have been dried over sodium sulfate
  3. customthe solvent is stripped off in a rotary evaporator
  4. customthe crude product is purified by column chromatography on silica gel (n-heptane/ethyl acetate 98:2)

Quellen und Nachweise

ORD-Eintrag
ord-d186617ecc044e7e8fe8929a61fdfec6
Quelldatensatz
uspto-grants-2013_03
Patentnummer
US08399509B2

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