Nitrogen → N-(5-nitrobiphenyl-3-yl)acetamide

HRID 64130

Reaktionsgleichung

Reaktionsgleichung von HRID 64130
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.[C:17]1(B(O)O)[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.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]>[N+:8]([C:6]1[CH:5]=[C:4]([NH:11][C:12](=[O:14])[CH3:13])[CH:3]=[C:2]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:7]=1)([O-:10])=[O:9]

Komponenten

7

Edukt 4

HCID 947NitrogenHCID 10340Sodium CarbonateHCID 66827Phenylboronic AcidHCID 10658908N-(3-bromo-5-nitrophenyl)acetamide

Produkt 1

HCID 89500237N-(5-nitrobiphenyl-3-yl)acetamideAusbeute 61 %

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) (1 g, 3.87 mmol) in 1,2-dimethoxyethane (20 ml) was degassed by N2 bubbling for 5 min. Phenyl-boronic acid (0.61 g, 5.04 mmol, 1.3 eq.) was added and the mixture was degassed for another 5 min. Pd(dppf)Cl2 (0.63 g, 0.77 mmol, 0.2 eq.) and aqueous sodium carbonate (1.23 g, 11.6 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, 50% ethyl acetate in hexane) to give the product in 61% 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, 50% ethyl acetate in hexane)
  3. customto give the product in 61% yield (0.6 g)

Quellen und Nachweise

ORD-Eintrag
ord-d7937579df9c41098c17dc381f3d5ca0
Quelldatensatz
uspto-grants-2016_09
Patentnummer
US09447091B2

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