Nitrogen → N-(2',6'-difluoro-5-nitrobiphenyl-3-yl)acetamide

HRID 64136

Reaktionsgleichung

Reaktionsgleichung von HRID 64136
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:23]=[CH:22][CH:21]=[C:20]([F:24])[C:19]=1B(O)O.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:23]=[CH:22][CH:21]=[C:20]([F:24])[C:19]=1[C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[C:4]([NH:11][C:12](=[O:14])[CH3:13])[CH:3]=1

Komponenten

7

Edukt 4

HCID 947NitrogenHCID 10340Sodium CarbonateHCID 27343362,6-Difluorophenylboronic acidHCID 10658908N-(3-bromo-5-nitrophenyl)acetamide

Produkt 1

HCID 117777574N-(2',6'-difluoro-5-nitrobiphenyl-3-yl)acetamideAusbeute 94 %

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) (20 g, 77 mmol) in 1,2-dimethoxyethane (250 ml) was degassed by N2 bubbling for 5 min. 2,6-Difluorophenylboronic acid (14.6 g, 92.4 mmol, 1.2 eq.) was added and the mixture was degassed for another 5 min. Pd(dppf)Cl2 (6.28 g, 7.7 mmol, 0.1 eq.) and aqueous sodium carbonate (24.49 g, 231 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, 30% ethyl acetate in hexane) to give the product in 94% yield (21.2 g). LC-MS (ESI): Calculated mass: 292.24; Observed mass: 293.1 [M+H]+ (rt: 1.49 min).

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, 30% ethyl acetate in hexane)
  3. customto give the product in 94% yield (21.2 g)
  4. custom293.1 [M+H]+ (rt: 1.49 min)

Quellen und Nachweise

ORD-Eintrag
ord-0ae67e8e08ca44d498ab0dcc2f7cbd43
Quelldatensatz
uspto-grants-2016_09
Patentnummer
US09447091B2

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