2-Pyridinamine, N-methyl- → N,6-dimethyl-N-pyridin-2-ylpyridin-2-amine

HRID 1926503

Reaktionsgleichung

Reaktionsgleichung von HRID 1926503
[CH3:1][NH:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][N:4]=1.Br[C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([CH3:16])[N:11]=1.CC(C)([O-])C.[Na+]>C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2].C1(C)C=CC=CC=1>[CH3:1][N:2]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][N:4]=1)[C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([CH3:16])[N:11]=1

Komponenten

6

Edukt 3

HCID 207272-Pyridinamine, N-methyl-HCID 792052-Bromo-6-methylpyridineHCID 23676156Sodium t-butoxide

Produkt 1

HCID 66628284N,6-dimethyl-N-pyridin-2-ylpyridin-2-amineAusbeute 95 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)KatalysatorHCID 1140TolueneLösungsmittel

Versuchsvorschrift

To a flask were added 0.75 g 2-(methylamino)pyridine, 1.0 g 2-bromo-6-methylpyridine, 0.95 g sodium tert-butoxide, 0.16 g 1,1′-bis(diphenylphosphino)ferrocene and 50 ml toluene. The mixture was purged thoroughly with nitrogen and 0.14 g of tris(dibenzylideneacetone)d2-propanollladium(0) was added and the mixture was heated to 80 C under nitrogen for 16 hours. After cooling to 22 C and quenching with 50 ml water, the product was extracted twice with ethyl acetate and washed twice with water. After filtration and solvent removal, the product was purified by silica gel chromatography using 35% ethyl acetate in hexane resulting in an orange oil. This was dissolved in 75 ml tert-butyl methyl ether and extracted into 75 ml 1M hydrochloric acid. After basification with 3M sodium hydroxide solution, the product was extracted with 75 ml tert-butyl methyl ether. Following removal of solvent, 1.1 g of a yellow oil was obtained.

Aufarbeitung

  1. customThe mixture was purged thoroughly with nitrogen and 0.14 g of tris(dibenzylideneacetone)d2-propanollladium(0)
  2. additionwas added
  3. temperaturethe mixture was heated to 80 C under nitrogen for 16 hours
  4. temperatureAfter cooling to 22 C
  5. customquenching with 50 ml water
  6. extractionthe product was extracted twice with ethyl acetate
  7. washwashed twice with water
  8. filtrationAfter filtration and solvent removal
  9. customthe product was purified by silica gel chromatography
  10. dissolutionThis was dissolved in 75 ml tert-butyl methyl ether
  11. extractionextracted into 75 ml 1M hydrochloric acid
  12. extractionAfter basification with 3M sodium hydroxide solution, the product was extracted with 75 ml tert-butyl methyl ether
  13. customremoval of solvent

Quellen und Nachweise

ORD-Eintrag
ord-b7719d2782784fed91cbf206e52a0e77
Quelldatensatz
uspto-grants-2012_05
Patentnummer
US08182718B2

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