Nitrogen → N-(3',4'-difluoro-5-nitrobiphenyl-3-yl)acetamide

HRID 64135

Reaktionsgleichung

Reaktionsgleichung von HRID 64135
Br[C:2]1[CH:3]=[C:4]([NH:11][C:12](=[O:14])[CH3:13])[CH:5]=[C:6]([N+:8]([O-:10])=[O:9])[CH:7]=1.N#N.[F:17][C:18]1[CH:19]=[C:20](B(O)O)[CH:21]=[CH:22][C:23]=1[F:24].C(=O)([O-])[O-].[Na+].[Na+]>COCCOC.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[F:17][C:18]1[CH:19]=[C:20]([C:2]2[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[C:4]([NH:11][C:12](=[O:14])[CH3:13])[CH:3]=2)[CH:21]=[CH:22][C:23]=1[F:24]

Komponenten

7

Edukt 4

HCID 947NitrogenHCID 10340Sodium CarbonateHCID 27343373,4-Difluorobenzeneboronic acidHCID 10658908N-(3-bromo-5-nitrophenyl)acetamide

Produkt 1

HCID 117777845N-(3',4'-difluoro-5-nitrobiphenyl-3-yl)acetamideAusbeute 76 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)KatalysatorHCID 80711,2-DimethoxyethaneLösungsmittel

Versuchsvorschrift

A solution of N-(3-bromo-5-nitrophenyl)acetamide of Example 1(c) (0.7 g, 2.69 mmol) in 1,2-dimethoxyethane (15 ml) was degassed by N2 bubbling for 5 min. 3,4-Difluorophenylboronic acid (0.5 g, 3.23 mmol, 1.2 eq.) was added and the mixture was degassed for another 5 min. Pd(dppf)Cl2 (0.44 g, 0.54 mmol, 0.2 eq.) and aqueous sodium carbonate (0.86 g, 8.07 mmol, 3.0 eq.) were added and the procedure of Example 1(d) was followed. The crude residue of the product was purified by column chromatography (60-120 silica gel, 25% ethyl acetate in hexane) to give the product in 76% yield (0.6 g).

Aufarbeitung

  1. customthe mixture was degassed for another 5 min
  2. customThe crude residue of the product was purified by column chromatography (60-120 silica gel, 25% ethyl acetate in hexane)
  3. customto give the product in 76% yield (0.6 g)

Quellen und Nachweise

ORD-Eintrag
ord-06b0436da7f34efaaf0a773e31cd3b07
Quelldatensatz
uspto-grants-2016_09
Patentnummer
US09447091B2

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