Reaktion #356684

ord-69dd17d9e2724ff79096b64984e8a2a4

Reaktionsgleichung

O=C(Cl)Cc1cccc(F)c1F
2,3-Difluorophenylacetyl chloride
Brc1cnc2[nH]ccc2c1
5-bromo-1H-pyrrolo[2,3-b]pyridine
[Al+3].[Cl-].[Cl-].[Cl-]
AlCl3
O=C(Cc1cccc(F)c1F)c1c[nH]c2ncc(Br)cc12
title compound
Ausbeute 98.4%
O=C(Cc1cccc(F)c1F)c1c[nH]c2ncc(Br)cc12
1-(5-Bromo-1H-pyrrolo[2,3-b]pyridin-3-yl)-2-(2,3-difluoro-phenyl)-ethanone
Ausbeute 98.4%

Lösungsmittel

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    workup.ADDITIONAfter the addition
  2. 2
    Sonstigethe cooling bath was removed
  3. 3
    TemperaturThe reaction was cooled with ice-bath
  4. 4
    workup.ADDITIONmethanol (100 ml) was added to the reaction mixture
  5. 5
    Temperaturwhile maintaining the temperature below 30° C
  6. 6
    SonstigeThe reaction mixture was evaporated
  7. 7
    FiltrationThe solid was collected by vacuum filtration
  8. 8
    Waschenwashed with water and hexane

Vorschrift

2,3-Difluorophenylacetyl chloride(58.1 mmol) in CH2Cl2 (150 ml)was added to a suspension of 5-bromo-1H-pyrrolo[2,3-b]pyridine (8.0 g, 40.6 mmol) and AlCl3 (46 g, 345 mmol) in CH2Cl2 (100 ml) at 0° C. After the addition, the cooling bath was removed and the reaction mixture was stirred at room temperature for 1.5 hrs. The reaction was cooled with ice-bath and methanol (100 ml) was added to the reaction mixture while maintaining the temperature below 30° C. The reaction mixture was evaporated and the residue was suspended in water. The solid was collected by vacuum filtration, washed with water and hexane to give the title compound (14.03 g) in 98% yield.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US07446199B2uspto-grants-2008_11