Tetrabutylammonium Fluoride → 4-Azaindole

HRID 400607

Reaktionsgleichung

Reaktionsgleichung von HRID 400607
C(OC(=O)[NH:7][C:8]1[C:9]([C:14]#[C:15][Si](C)(C)C)=[N:10][CH:11]=[CH:12][CH:13]=1)(C)(C)C.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1.C(OCC)C>[NH:7]1[C:8]2[C:9](=[N:10][CH:11]=[CH:12][CH:13]=2)[CH:14]=[CH:15]1

Komponenten

5

Edukt 2

HCID 2724141Tetrabutylammonium FluorideHCID 60026792(2-Trimethylsilanylethynylpyridin-3-yl)carbamic acid tert-butyl ester

Produkt 1

HCID 92264-AzaindoleAusbeute 79 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3283Diethyl EtherLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A mixture of (2-trimethylsilanylethynylpyridin-3-yl)carbamic acid tert-butyl ester (500 mg, 1.72 mmol) in 5 mL of THF was treated with TBAF (1 M in THF, 10.3 mL) at room temperature. The mixture was heated at reflux for 8 hours, cooled to room temperature, diluted with 100 mL of diethyl ether, and quenched with 100 mL of water. The aqueous layer was extracted with three 50 mL portions of diethyl ether, and the combined organic layers were washed with 500 mL of brine, dried over magnesium sulfate, filtered, and concentrated in vacuo. Chromatography on SiO2 (100% CH2Cl2 to 10% MeOH in CH2Cl2, gradient) gave 160 mg of the title product as tan solid (79% yield).

Aufarbeitung

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 8 hours
  3. customquenched with 100 mL of water
  4. extractionThe aqueous layer was extracted with three 50 mL portions of diethyl ether
  5. washthe combined organic layers were washed with 500 mL of brine
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-0d405b098db34ff5a7fb26c0e1577e39
Quelldatensatz
uspto-grants-2014_06
Patentnummer
US08741897B2

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