2-Bromo-6-methylpyridine → 2-methyl-N-(6-methylpyridin-2-yl)quinolin-8-amine

HRID 495274

Reaktionsgleichung

Reaktionsgleichung von HRID 495274
[CH3:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[C:5]([NH2:12])[CH:6]=[CH:7][CH:8]=2)[N:3]=1.[CH3:13][C:14]1[N:19]=[C:18](Br)[CH:17]=[CH:16][CH:15]=1.CC(C)([O-])C.[Na+]>C1(C)C=CC=CC=1>[CH3:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[C:5]([NH:12][C:18]3[CH:17]=[CH:16][CH:15]=[C:14]([CH3:13])[N:19]=3)[CH:6]=[CH:7][CH:8]=2)[N:3]=1

Komponenten

5

Edukt 3

HCID 792052-Bromo-6-methylpyridineHCID 1404572-Methyl-8-aminoquinolineHCID 23676156Sodium t-butoxide

Produkt 1

HCID 666278362-methyl-N-(6-methylpyridin-2-yl)quinolin-8-amineAusbeute 68 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

To a flask were added 4.2 g of 2-methylquinolin-8-amine, 4.6 g of 6-methyl-2-bromopyridine, 3.3 g of sodium tert-butoxide, and 75 ml toluene. The mixture was purged thoroughly with nitrogen and 44 mg of 1,1′-bis(diphenylphosphino)ferrocene and 18 mg of palladium acetate were added. The reaction mixture was heated to 80 C for 16 hours, and then cooled to 22 C. After quenching with 100 ml of water, the product was extracted with 75 ml ethyl acetate. The product was extracted with 120 ml of 1M hydrochloric acid, and then basified with 3M sodium hydroxide. Following extraction with 75 ml of ethyl acetate and washing with 30 ml of water, the solvent was removed. The product was purified by dissolving in a hot mixture of 20 ml of 2-propanol and 5 ml of water, and after cooling to 5 C, the product was filtered, washed with 50% 2-propanol, and dried, resulting in 4.5 g of a tan solid.

Aufarbeitung

  1. customThe mixture was purged thoroughly with nitrogen and 44 mg of 1,1′-bis(diphenylphosphino)ferrocene and 18 mg of palladium acetate
  2. additionwere added
  3. temperatureThe reaction mixture was heated to 80 C for 16 hours
  4. temperaturecooled to 22 C
  5. customAfter quenching with 100 ml of water
  6. extractionthe product was extracted with 75 ml ethyl acetate
  7. extractionThe product was extracted with 120 ml of 1M hydrochloric acid
  8. extractionextraction with 75 ml of ethyl acetate
  9. washwashing with 30 ml of water
  10. customthe solvent was removed
  11. customThe product was purified
  12. dissolutionby dissolving in a hot mixture of 20 ml of 2-propanol and 5 ml of water
  13. temperatureafter cooling to 5 C
  14. filtrationthe product was filtered
  15. washwashed with 50% 2-propanol
  16. customdried

Quellen und Nachweise

ORD-Eintrag
ord-6f70af42f03e41db914acb020bc5968d
Quelldatensatz
uspto-grants-2009_05
Patentnummer
US07538931B2

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