Potassium Carbonate → 6-bromo-1-[1-(2,6-dichloro-3-fluorophenyl)ethoxy]-1H-pyrrolo[3,2-b]pyridine

HRID 1404579

Reaktionsgleichung

Reaktionsgleichung von HRID 1404579
CS([O:5][CH:6]([C:8]1[C:13]([Cl:14])=[CH:12][CH:11]=[C:10]([F:15])[C:9]=1[Cl:16])[CH3:7])(=O)=O.[Br:17][C:18]1[CH:19]=[C:20]([N+:35]([O-])=O)[C:21]([CH:24](C(OCC)=O)[C:25](OCC)=O)=[N:22][CH:23]=1.C([O-])([O-])=O.[K+].[K+]>CN(C)C=O>[Br:17][C:18]1[CH:19]=[C:20]2[N:35]([O:5][CH:6]([C:8]3[C:13]([Cl:14])=[CH:12][CH:11]=[C:10]([F:15])[C:9]=3[Cl:16])[CH3:7])[CH:25]=[CH:24][C:21]2=[N:22][CH:23]=1

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 57516275HCID 57516275, VerbindungHCID 585324961-(2,6-Dichloro-3-fluorophenyl)ethyl methanesulfonate

Produkt 1

HCID 674584186-bromo-1-[1-(2,6-dichloro-3-fluorophenyl)ethoxy]-1H-pyrrolo[3,2-b]pyridineAusbeute 78 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A solution of 1-(2,6-dichloro-3-fluorophenyl)ethyl methanesulfonate (4.39 g, 15.3 mmol, 1.0 eq), 6-bromo-1H-pyrrolo[3,2-b]pyridin-1-ol (prepared as in example 1: 3.92 g, 20.0 mmol, 1.3 eq) and K2CO3 (6.34 g, 45.9 mmol, 3.0 eq) in 90 ml of N,N-dimethylformamide (DMF) was stirred at room temperature overnight. The solid was filtered out and the solvent evaporated. The residue was dissolved in DCM, and the solution was washed with water and brine, dried, evaporated and chromatographed (MeOH/DCM 1:20) to give a light yellow oil, 4.63 g, in 78% yield.

Aufarbeitung

  1. filtrationThe solid was filtered out
  2. customthe solvent evaporated
  3. dissolutionThe residue was dissolved in DCM
  4. washthe solution was washed with water and brine
  5. customdried
  6. customevaporated
  7. customchromatographed (MeOH/DCM 1:20)
  8. customto give a light yellow oil, 4.63 g

Quellen und Nachweise

ORD-Eintrag
ord-b14a655b409c405baae399dddaf72956
Quelldatensatz
uspto-grants-2014_12
Patentnummer
US08912330B2

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