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Potassium Phosphate, Tribasic → Ethyl 5-fluoro-1-(4,6-dimethylpyridin-2-yl)-1H-indole-2-carboxylate

HRID 252192
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 252192
[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:5]2.Br[C:17]1[CH:22]=[C:21]([CH3:23])[CH:20]=[C:19]([CH3:24])[N:18]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].CNC1CCCCC1NC>[Cu](I)I.C(OCC)(=O)C.C(O)(=O)C.O.C1(C)C=CC=CC=1>[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([C:17]1[CH:22]=[C:21]([CH3:23])[CH:20]=[C:19]([CH3:24])[N:18]=1)[C:6]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:5]2
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

10

Edukt 4

HCID 62657Potassium Phosphate, TribasicHCID 5510741-N,2-N-dimethylcyclohexane-1,2-diamineHCID 2727899ethyl 5-fluoro-1H-indole-2-carboxylateHCID 149751952-Bromo-4,6-dimethylpyridine

Produkt 1

HCID 66845370Ethyl 5-fluoro-1-(4,6-dimethylpyridin-2-yl)-1H-indole-2-carboxylateAusbeute 84,8 %

Reagenzien, Katalysatoren, Lösungsmittel

5
HCID 83717Copper iodideKatalysatorHCID 176Acetic AcidLösungsmittelHCID 962WaterLösungsmittelHCID 1140TolueneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
110 °C

Versuchsvorschrift

4.35 g (21 mmol) of ethyl 5-fluoro-1H-indole-2-carboxylate, 4.29 g (23.1 mmol) of 2-bromo-4,6-dimethylpyridine, 9.36 g (44.1 mmol) of tripotassium phosphate, 0.66 ml (4.2 mmol) of 1,2-dimethylaminocyclohexane, 0.2 g (1.05 mmol) of copper iodide and 21 ml of dry toluene are added to a pressure tube. The tube is closed and the reaction mixture is stirred at 110° C. for 5 days. After this time, the mixture is poured onto a solution of 100 ml of water and the pH of the medium is adjusted to pH 5 by additions of acetic acid. 100 ml of ethyl acetate are added. The organic phase is separated, washed successively with 50 ml of water and 50 ml of a saturated aqueous sodium chloride solution, then dried over sodium sulfate, filtered and then concentrated under reduced pressure. The residue is purified by preparative chromatography (eluent: dichloromethane/ethyl acetate). 5.56 g of expected product are obtained, which product is used as is in the continuation of the synthesis.

Aufarbeitung

  1. customThe tube is closed
  2. customThe organic phase is separated
  3. washwashed successively with 50 ml of water and 50 ml of a saturated aqueous sodium chloride solution
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue is purified by preparative chromatography (eluent: dichloromethane/ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-f53d76a0370940489ad956c4b9377b92
Quelldatensatz
uspto-grants-2011_01
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07868024B2

Notizen zur Reaktion

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