Tetrabutylammonium Fluoride → 5-Chloro-1H-pyrrolo[2,3-b]pyridine

HRID 1786764Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1786764
[Cl:1][C:2]1[CH:3]=[C:4]2[CH:10]=[C:9]([Si](CC)(CC)CC)[NH:8][C:5]2=[N:6][CH:7]=1.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1.C(OCC)(=O)C>[Cl:1][C:2]1[CH:3]=[C:4]2[CH:10]=[CH:9][NH:8][C:5]2=[N:6][CH:7]=1

Komponenten

5

Edukt 2

HCID 2724141Tetrabutylammonium FluorideHCID 57774343HCID 57774343, Verbindung

Produkt 1

HCID 242292135-Chloro-1H-pyrrolo[2,3-b]pyridineAusbeute 90 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

Compound 41 (4.37 g, 0.0164 mol) was dissolved in THF. Molecular sieve (10 g of 3A) was added followed by TBAF (32.75 mL, 0.0328). The reaction mixture was stirred for 5 h at rt. Diluted with ethyl acetate and washed several times with water, brine and the organic layer was dried and concentrated in vacuo to an oil that was subjected to flash chromatography (30% EtOAc-70% hexanes) to give 02.3 g (90%) of the desired material 42. 1H NMR DMSO d6 11.8 (bs, 1H), 8.2 (s, 1H), 8.1 (s, 1H), 7.5 (s, 1H), 6.5 (s, 1H).

Aufarbeitung

  1. washwashed several times with water, brine
  2. customthe organic layer was dried
  3. concentrationconcentrated in vacuo to an oil that

Quellen und Nachweise

ORD-Eintrag
ord-3a668e086f9d4af2aefd449954e6ab0e
Quelldatensatz
uspto-grants-2009_03
Patentnummer
US07507826B2

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