Water → Ethanone, 2-bromo-1-(4-fluoro-1H-pyrrolo[2,3-b]pyridin-3-yl)-

HRID 2108735Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2108735
[F:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[NH:8][CH:9]=[CH:10][C:3]=12.[Cl-].[Al+3].[Cl-].[Cl-].[Br:15][CH2:16][C:17](Br)=[O:18].O>ClCCl>[Br:15][CH2:16][C:17]([C:10]1[C:3]2[C:4](=[N:5][CH:6]=[CH:7][C:2]=2[F:1])[NH:8][CH:9]=1)=[O:18]

Komponenten

6

Edukt 4

HCID 962WaterHCID 61147Bromoacetyl bromideHCID 6451240Aluminum(III) ChlorideHCID 112979984-Fluoro-1H-pyrrolo(2,3-b)pyridine

Produkt 1

HCID 57421973Ethanone, 2-bromo-1-(4-fluoro-1H-pyrrolo[2,3-b]pyridin-3-yl)-

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of 4-fluoro-1H-pyrrolo[2,3-b]pyridine (2.00 g, 0.0147 mol) (Org. Lett., 2003, 5, 5023-5025) in dichloromethane was added aluminum chloride (3.92 g, 0.0294 mol) in portions, the mixture was stirred at RT for 30 min, then bromoacetyl bromide (4.45 g, 0.022 mol) was added dropwise. The reaction mixture was stirred at 50° C. for 1 h, when TLC indicated no starting material. To the reaction mixture was added 150 mL water, and the resulting suspension was heated at 100° C. for 1 h, then filtered to afford the desired product, 90% pure. H NMR, DMSO-d6: 4.72(s, 2H), 7.12(m, 1H), 8.36(m, 1H), 8.67(s, 1H).

Aufarbeitung

  1. stirringThe reaction mixture was stirred at 50° C. for 1 h
  2. temperaturethe resulting suspension was heated at 100° C. for 1 h
  3. filtrationfiltered

Quellen und Nachweise

ORD-Eintrag
ord-f43fced1acc84e01a9a38feb9f7b5cd7
Quelldatensatz
uspto-grants-2009_04
Patentnummer
US07514448B2

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