Benzophenone imine → 6-chloro-N-(diphenylmethylidene)-4-methylpyridin-2-amine

HRID 1504771Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1504771
CC(C)([O-])C.[Na+].[C:7](=[NH:20])([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[Cl:21][C:22]1[CH:27]=[C:26]([CH3:28])[CH:25]=[C:24](Cl)[N:23]=1>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C1(C)C=CC=CC=1>[Cl:21][C:22]1[N:23]=[C:24]([N:20]=[C:7]([C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:25]=[C:26]([CH3:28])[CH:27]=1

Komponenten

6

Edukt 3

HCID 136809Benzophenone imineHCID 108989972,6-Dichloro-4-methylpyridineHCID 23676156Sodium t-butoxide

Produkt 1

HCID 867316646-chloro-N-(diphenylmethylidene)-4-methylpyridin-2-amine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 9811564Bis(dibenzylideneacetone)palladiumKatalysatorHCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

Toluene (27 mL), sodium tert-butoxide (0.925 g, 9.63 mmol), and benzophenone imine (1.75 g, 9.63 mmol) were added to 2,6-dichloro-4-methylpyridine (1.3 g, 8.0 mmol). The flask was purged with argon 3 times before 2-dicyclophenylphosphino-2′-(N,N-dimethylamino)biphenyl (0.474 g, 1.20 mmol) and Pd2(dba)3 (0.367 g, 0.401 mmol) were added. The flask was purged 3 times with argon, sealed, and heated to 80° C. After 16 hours, the reaction mixture was cooled to room temperature, diluted with water, and extracted with DCM. The organic layer was dried over sodium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by silica gel chromatography (0-40% acetone/hexanes, linear gradient) to afford 6-chloro-N-(diphenylmethylidene)-4-methylpyridin-2-amine. 1H NMR (500 MHz, CDCl3) δ 7.83-7.73 (m, 2H), 7.49 (t, J=7.6 Hz, 2H), 7.44-7.34 (m, 2H), 7.34-7.27 (m, 2H), 7.21-7.12 (m, 2H), 6.72 (s, 1H), 6.27 (s, 1H), 2.15 (s, 3H).

Aufarbeitung

  1. additionwere added
  2. customThe flask was purged 3 times with argon
  3. customsealed
  4. temperaturethe reaction mixture was cooled to room temperature
  5. additiondiluted with water
  6. extractionextracted with DCM
  7. dry with materialThe organic layer was dried over sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure
  10. customThe residue was purified by silica gel chromatography (0-40% acetone/hexanes, linear gradient)

Quellen und Nachweise

ORD-Eintrag
ord-201cd0aef27240b7a4b1a94c1e6a7676
Quelldatensatz
uspto-grants-2015_12
Patentnummer
US09216173B2

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