Potassium Fluoride → N-(5-((5-bromo-3-nitropyridin-2-yl)amino)-2',6'-difluoro-[1,1'-biphenyl]-3-yl)acetamide

HRID 64150

Reaktionsgleichung

Reaktionsgleichung von HRID 64150
[NH2:1][C:2]1[CH:3]=[C:4]([NH:16][C:17](=[O:19])[CH3:18])[CH:5]=[C:6]([C:8]2[C:13]([F:14])=[CH:12][CH:11]=[CH:10][C:9]=2[F:15])[CH:7]=1.[Br:20][C:21]1[CH:22]=[C:23]([N+:28]([O-:30])=[O:29])[C:24](Cl)=[N:25][CH:26]=1.[F-].[K+]>CN(C=O)C>[Br:20][C:21]1[CH:22]=[C:23]([N+:28]([O-:30])=[O:29])[C:24]([NH:1][C:2]2[CH:3]=[C:4]([NH:16][C:17](=[O:19])[CH3:18])[CH:5]=[C:6]([C:8]3[C:13]([F:14])=[CH:12][CH:11]=[CH:10][C:9]=3[F:15])[CH:7]=2)=[N:25][CH:26]=1

Komponenten

5

Edukt 3

HCID 522689Potassium FluorideHCID 70194125-Bromo-2-chloro-3-nitropyridineHCID 89500157N-(5-amino-2',6'-difluoro-[1,1'-biphenyl]-3-yl)acetamide

Produkt 1

HCID 117777719N-(5-((5-bromo-3-nitropyridin-2-yl)amino)-2',6'-difluoro-[1,1'-biphenyl]-3-yl)acetamideAusbeute 28 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A solution of N-(5-amino-2′,6′-difluoro-[1,1′-biphenyl]-3-yl)acetamide (1.4 g, 6.1 mmol), 5-bromo-2-chloro-3-nitropyridine (1.6 g, 6.1 mmol, 1.0 eq.) and potassium fluoride (0.53 g, 9.0 mmol, 1.5 eq.) in DMF (8 ml) was heated at 110° C. for 4 h. The mixture was quenched and extracted as in Example 1(d). The solvent was distilled off to afford the crude product which was purified by column chromatography (60-120 silica gel, 30% Ethyl acetate in hexane) to give the title product in 28% yield (0.8 g).

Aufarbeitung

  1. customThe mixture was quenched
  2. extractionextracted as in Example 1(d)
  3. distillationThe solvent was distilled off
  4. customto afford the crude product which
  5. customwas purified by column chromatography (60-120 silica gel, 30% Ethyl acetate in hexane)

Quellen und Nachweise

ORD-Eintrag
ord-617f241a9e4c4fe1aee17f66a38e319f
Quelldatensatz
uspto-grants-2016_09
Patentnummer
US09447091B2

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