Water → Ethyl 1-(3-isopropylphenyl)-5-trifluoromethyloxy-1H-indole-2-carboxylate

HRID 505630Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 505630
[F:1][C:2]([F:19])([F:18])[O:3][C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][C:8]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:7]2.[CH:20]([C:23]1[CH:24]=[C:25](B(O)O)[CH:26]=[CH:27][CH:28]=1)([CH3:22])[CH3:21].N1C=CC=CC=1.O>ClCCl.C([O-])(=O)C.C([O-])(=O)C.[Cu+2]>[CH:20]([C:23]1[CH:28]=[C:27]([N:9]2[C:10]3[C:6](=[CH:5][C:4]([O:3][C:2]([F:1])([F:18])[F:19])=[CH:12][CH:11]=3)[CH:7]=[C:8]2[C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH:26]=[CH:25][CH:24]=1)([CH3:22])[CH3:21]

Komponenten

7

Edukt 4

HCID 962WaterHCID 1049PyridineHCID 2737230ethyl 5-(trifluoromethoxy)-1H-indole-2-carboxylateHCID 27734783-Isopropylbenzeneboronic acid

Produkt 1

HCID 68698882Ethyl 1-(3-isopropylphenyl)-5-trifluoromethyloxy-1H-indole-2-carboxylateAusbeute 35 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8895Cupric acetateKatalysatorHCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

A mixture of 0.2 g (0.73 mmol) of ethyl 5-trifluoromethyloxy-1H-indole-2-carboxylate, of 0.24 g (1.46 mmol) of 3-isopropylphenylboronic acid, of 0.2 g (1.1 mmol) of copper diacetate and of 0.12 ml (1.46 mmol) of pyridine in 5 ml of dichloromethane is stirred in the presence of 4 Å molecular sieve at ambient temperature for 4 days. The mixture is poured onto 100 ml of water and 50 ml of dichloromethane. The organic phase is separated, washed with 1N hydrochloric acid, dried over magnesium sulfate and then concentrated under reduced pressure. The residue is purified by chromatography on a silica column, elution being carried out with a mixture of cyclohexane and of ethyl acetate. 0.1 g of product is obtained, which product is used as is in the following stage.

Aufarbeitung

  1. customThe organic phase is separated
  2. washwashed with 1N hydrochloric acid
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue is purified by chromatography on a silica column, elution
  6. additionbeing carried out with a mixture of cyclohexane and of ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-92ce70887862486b9c6ac3d16176b4a8
Quelldatensatz
uspto-grants-2010_08
Patentnummer
US07781477B2

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