3-Methyl-2-(tributylstannyl)pyridine → 4-Chloro-5,7-difluoro-3-methyl-2-(3-methylpyridin-2-yl)quinoline

HRID 1431401Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1431401
Cl[C:2]1[C:11]([CH3:12])=[C:10]([Cl:13])[C:9]2[C:4](=[CH:5][C:6]([F:15])=[CH:7][C:8]=2[F:14])[N:3]=1.[CH3:16][C:17]1[C:18]([Sn](CCCC)(CCCC)CCCC)=[N:19][CH:20]=[CH:21][CH:22]=1>C1(C)C=CC=CC=1>[Cl:13][C:10]1[C:9]2[C:4](=[CH:5][C:6]([F:15])=[CH:7][C:8]=2[F:14])[N:3]=[C:2]([C:18]2[C:17]([CH3:16])=[CH:22][CH:21]=[CH:20][N:19]=2)[C:11]=1[CH3:12]

Komponenten

4

Edukt 2

HCID 164270983-Methyl-2-(tributylstannyl)pyridineHCID 596310402,4-Dichloro-5,7-difluoro-3-methylquinoline

Produkt 1

HCID 596311854-Chloro-5,7-difluoro-3-methyl-2-(3-methylpyridin-2-yl)quinoline

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

To a stirred solution of 2,4-dichloro-5,7-difluoro-3-methylquinoline (0.17 g, 0.685 mmol) in toluene (1.40 mL) was added 3-methyl-2-(tributylstannyl)pyridine (0.29 g, 0.75 mmol), and palladium tetrakistriphenylphosphine (0.079 g, 0.069 mmol). The reaction was stirred at 100° C. and stirring continued for 68 h. The reaction mixture was cooled to rt and concentrated in vacuo. The crude material was purified by column chromatography on silica gel, eluting with (0-50% EtOAc in hexanes) to provide 4-chloro-5,7-difluoro-3-methyl-2-(3-methylpyridin-2-yl)quinoline as a white solid. Mass Spectrum (ESI) m/e=305.0 (M+1).

Aufarbeitung

  1. stirringstirring
  2. temperatureThe reaction mixture was cooled to rt
  3. concentrationconcentrated in vacuo
  4. customThe crude material was purified by column chromatography on silica gel
  5. washeluting with (0-50% EtOAc in hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-118495e4aa124836832a2cca45f64183
Quelldatensatz
uspto-grants-2015_01
Patentnummer
US08940724B2

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