Triethylsilane → Methyl 2-(1H-pyrrolo[2,3-b]pyridin-3-yl)acetate

HRID 1036627Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1036627
C([SiH](CC)CC)C.O=[C:9]([C:14]1[C:22]2[C:17](=[N:18][CH:19]=[CH:20][CH:21]=2)[NH:16][CH:15]=1)[C:10]([O:12][CH3:13])=[O:11]>C(O)(C(F)(F)F)=O>[NH:16]1[C:17]2=[N:18][CH:19]=[CH:20][CH:21]=[C:22]2[C:14]([CH2:9][C:10]([O:12][CH3:13])=[O:11])=[CH:15]1

Komponenten

4

Edukt 2

HCID 12052TriethylsilaneHCID 6028556Methyl 7-azaindole-3-glyoxylate

Produkt 1

HCID 25067325Methyl 2-(1H-pyrrolo[2,3-b]pyridin-3-yl)acetateAusbeute 75,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6422Trifluoroacetic acidLösungsmittel

Versuchsvorschrift

To a mixture of triethylsilane (9.95 g, 85.78 mmol) in TFA (25 mL) was added portionwise methyl oxo(1H-pyrrolo[2,3-b]pyridin-3-yl)acetate (5.0 g, 24.48 mmol). After a period of 18 h at 50° C., the solvent was evaporated and saturated NaHCO3 was added followed by DCM. The organic phase was separated, dried over magnesium sulfate, filtered and evaporated under reduced pressure. The residue was purified by combiflash with 10% ethyl acetate in hexane to 100% ethyl acetate to provide 3.5 g of the title compound.

Aufarbeitung

  1. customthe solvent was evaporated
  2. additionsaturated NaHCO3 was added
  3. customThe organic phase was separated
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. customevaporated under reduced pressure
  7. customThe residue was purified by combiflash with 10% ethyl acetate in hexane to 100% ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-47bde9a8ad6748d9986c78ccbceaf641
Quelldatensatz
uspto-grants-2013_10
Patentnummer
US08546422B2

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