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

HRID 877931Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 877931
[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-]>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

4

Edukt 2

HCID 2724141Tetrabutylammonium FluorideHCID 57774343HCID 57774343, Verbindung

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

Compound 41 (4.37 g, 0.0164 mol) was dissolved in THE 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. additionwas added
  2. washwashed several times with water, brine
  3. customthe organic layer was dried
  4. concentrationconcentrated in vacuo to an oil that

Quellen und Nachweise

ORD-Eintrag
ord-eda493c3e43641b98ccce8dac6c1bde1
Quelldatensatz
uspto-grants-2015_03
Patentnummer
US08987454B2

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