Nitrogen → N-(3-(6-methoxypyridin-3-yl)-5-nitrophenyl)acetamide

HRID 64142

Reaktionsgleichung

Reaktionsgleichung von HRID 64142
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.[CH3:17][O:18][C:19]1[N:24]=[CH:23][C:22](B(O)O)=[CH:21][CH:20]=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]>[CH3:17][O:18][C:19]1[N:24]=[CH:23][C:22]([C:2]2[CH:3]=[C:4]([NH:11][C:12](=[O:14])[CH3:13])[CH:5]=[C:6]([N+:8]([O-:10])=[O:9])[CH:7]=2)=[CH:21][CH:20]=1

Komponenten

7

Edukt 4

HCID 947NitrogenHCID 10340Sodium CarbonateHCID 2734368(6-Methoxypyridin-3-yl)boronic acidHCID 10658908N-(3-bromo-5-nitrophenyl)acetamide

Produkt 1

HCID 117777422N-(3-(6-methoxypyridin-3-yl)-5-nitrophenyl)acetamideAusbeute 81 %

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 (1 g, 3.86 mmol) in 1,2-dimethoxyethane (20 ml) was degassed by N2 bubbling for 5 min. (6-Methoxypyridin-3-yl)boronic acid (0.77 g, 5.0 mmol, 1.3 eq.) was added and the mixture was degassed for 5 min. Pd(dppf)Cl2 (0.630 g, 0.77 mmol, 0.2 eq.) and aqueous sodium carbonate (1.23 g, 11.58 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, 40% ethyl acetate in hexane) to give the product in 81% yield (0.9 g).

Aufarbeitung

  1. additionwas added
  2. customthe mixture was degassed for 5 min
  3. customThe crude residue of the product was purified by column chromatography (60-120 silica gel, 40% ethyl acetate in hexane)
  4. customto give the product in 81% yield (0.9 g)

Quellen und Nachweise

ORD-Eintrag
ord-fb6aa7ef1ade44179475dea6b4cadbe6
Quelldatensatz
uspto-grants-2016_09
Patentnummer
US09447091B2

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