Bromide ion → 2-(6-bromo-1H-pyrrolo[2,3-b]pyridin-1-yl)(phenyl)methanone

HRID 253469Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 253469
[NH+:1]1([O-])[C:5]2=[N:6][CH:7]=[CH:8][CH:9]=[C:4]2[CH:3]=[CH:2]1.[C:11](Br)(=[O:18])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C[Si](C)(C)N[Si](C)(C)C.[Br-:29]>C1C=CC=CC=1>[Br:29][C:7]1[N:6]=[C:5]2[N:1]([C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=3[CH:11]=[O:18])[CH:2]=[CH:3][C:4]2=[CH:9][CH:8]=1

Komponenten

6

Edukt 4

HCID 259Bromide ionHCID 12056Benzoyl bromideHCID 13838HexamethyldisilazaneHCID 219590977-aza-1H-indole N-oxide

Produkt 1

HCID 866231352-(6-bromo-1H-pyrrolo[2,3-b]pyridin-1-yl)(phenyl)methanone

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 241BenzeneLösungsmittel2×

Versuchsvorschrift

1H-pyrrolo[2,3-b]pyridine-N-oxide (154, 500 mg, 3.72 mmol) was dissolved in 40 mL of dry benzene. In a separate dry flask, benzoyl bromide (2.5 equiv) and 1,1,1,3,3,3-hexamethyldisilazane (1.0 equiv) were combined in 20 mL of dry benzene. The bromide solution was added in 5 mL aliquots over 30 minutes to the reaction flask. The reaction was stirred at ambient temperature for two hours. It was then washed with 3×30 ml, NaHCO3 (aq., satd.) and 1×30 mL brine. The organic layer was dried over sodium sulfate and evaporated. The crude material was taken directly to the next step without further purification.

Aufarbeitung

  1. customIn a separate dry flask
  2. washIt was then washed with 3×30 ml, NaHCO3 (aq., satd.) and 1×30 mL brine
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. customevaporated
  5. customThe crude material was taken directly to the next step without further purification

Quellen und Nachweise

ORD-Eintrag
ord-8c0515b7fc5e4843b1d1600370e8882d
Quelldatensatz
uspto-grants-2011_01
Patentnummer
US07872018B2

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