Sodium Carbonate → 4-(Pyridin-4-yl)naphth-1-ylamine

HRID 1275001

Reaktionsgleichung

Reaktionsgleichung von HRID 1275001
Br[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([NH2:12])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[Na+].[Na+].[N:19]1[CH:24]=[CH:23][C:22](B(O)O)=[CH:21][CH:20]=1>COCCOC.O>[N:19]1[CH:24]=[CH:23][C:22]([C:2]2[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]([NH2:12])=[CH:4][CH:3]=2)=[CH:21][CH:20]=1

Komponenten

6

Edukt 3

HCID 10340Sodium CarbonateHCID 753034-Bromo-1-naphthylamineHCID 2734379(Pyridin-4-yl)boronic acid

Produkt 1

HCID 108570124-(Pyridin-4-yl)naphth-1-ylamineAusbeute 78,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 80711,2-DimethoxyethaneLösungsmittel

Versuchsvorschrift

A stirred suspension of 4-bromonaphth-1-ylamine (10 g, 45 mnmole) in 1,2-dimethoxyethane (400 ml) and water (100 ml) containing sodium carbonate (14 g) was flushed with argon for 0.3h. Tetrakis (triphenylphosphine)palladium (0) (2.75 g, 2.4 mmole) was added followed by 4-pyridylboronic acid (5.7 g, 46 mmole) and the mixture heated at reflux for 5 h. The mixture was concentrated in vacuo to a brown slurry and partitioned between dichloromethane and water. The aqueous was further extracted with dichloromethane and the combined organics dried (Na2SO4) and concentrated in vacuo to a brown solid (13.2 g). Purification of the solid by flash chromatography eluting with ethyl acetate afforded the title compound as a yellow crystalline solid (7.8 g, 78%).

Aufarbeitung

  1. customwas flushed with argon for 0.3h
  2. temperaturethe mixture heated
  3. temperatureat reflux for 5 h
  4. concentrationThe mixture was concentrated in vacuo to a brown slurry
  5. custompartitioned between dichloromethane and water
  6. extractionThe aqueous was further extracted with dichloromethane
  7. dry with materialthe combined organics dried (Na2SO4)
  8. concentrationconcentrated in vacuo to a brown solid (13.2 g)
  9. customPurification of the solid by flash chromatography
  10. washeluting with ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-911282e799734b42b8df1ac143936374
Quelldatensatz
uspto-grants-2000_12
Patentnummer
US06159979

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