Sodium Phosphate, Dibasic → Indole

HRID 467551

Reaktionsgleichung

Reaktionsgleichung von HRID 467551
Br[C:2]1NC=CN=1.C1(S([N:16]2[C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[C:18](B(O)O)=N2)(=O)=O)C=CC=CC=1.P([O-])([O-])(O)=O.[Na+].[Na+]>O1CCOCC1.O>[NH:16]1[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[CH:18]=[CH:2]1

Komponenten

6

Edukt 3

HCID 24203Sodium Phosphate, DibasicHCID 27732612-Bromo-1H-imidazoleHCID 679930421-(Phenylsulfonyl)-3-indazole boronic acid

Produkt 1

HCID 798Indole

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
110 °C

Versuchsvorschrift

A mixture of bromoimidazole Int-22a (98 mg, 0.20 mmol), 1-(phenylsulfonyl)-3-indazole boronic acid (73 mg, 0.24 mmol) and sodium hydrogen phosphate (86 mg, 0.61 mmol) in 1,4-dioxane (4 mL) and water (2 mL) at r.t. was purged with nitrogen gas for 5 min in a microwave vial. Tetrakistriphenylphosphorous palladium was added. The mixture was heated in a microwave reactor at 110° C. for 1 h. Water and ethyl acetate were added, and the layers were separated. The separated aqueous layer was extracted with ethyl acetate. The separated organic layer was dried (MgSO4) and filtered. The solvents were removed in vacuo and chromatographic purification (ethyl acetate-hexane) of the residue gave indole Int-22b (112 mg, 84%) as a colorless oil.

Aufarbeitung

  1. customwas purged with nitrogen gas for 5 min in a microwave vial
  2. additionTetrakistriphenylphosphorous palladium was added
  3. additionWater and ethyl acetate were added
  4. customthe layers were separated
  5. extractionThe separated aqueous layer was extracted with ethyl acetate
  6. dry with materialThe separated organic layer was dried (MgSO4)
  7. filtrationfiltered
  8. customThe solvents were removed in vacuo and chromatographic purification (ethyl acetate-hexane) of the residue

Quellen und Nachweise

ORD-Eintrag
ord-ccfc4e784b904792be7ac92fb7cd954b
Quelldatensatz
uspto-grants-2014_01
Patentnummer
US08623857B2

Verknüpfte Notizen

Wird geladen…