2-Fluoro-5-methylpyridine → N-(4-(3-bromopyridin-2-yloxy)phenyl)-5-methylpyridin-2-amine

HRID 473629Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 473629
[Br:1][C:2]1[C:3]([O:8][C:9]2[CH:15]=[CH:14][C:12]([NH2:13])=[CH:11][CH:10]=2)=[N:4][CH:5]=[CH:6][CH:7]=1.F[C:17]1[CH:22]=[CH:21][C:20]([CH3:23])=[CH:19][N:18]=1>CN1C(=O)CCC1.O>[Br:1][C:2]1[C:3]([O:8][C:9]2[CH:15]=[CH:14][C:12]([NH:13][C:17]3[CH:22]=[CH:21][C:20]([CH3:23])=[CH:19][N:18]=3)=[CH:11][CH:10]=2)=[N:4][CH:5]=[CH:6][CH:7]=1

Komponenten

5

Edukt 2

HCID 27746352-Fluoro-5-methylpyridineHCID 577562564-(3-Bromopyridin-2-yloxy)benzenamine

Produkt 1

HCID 59374189N-(4-(3-bromopyridin-2-yloxy)phenyl)-5-methylpyridin-2-amine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 13387N-methyl-2-pyrrolidoneLösungsmittel

Reaktionsbedingungen

Temperatur
170 °C

Versuchsvorschrift

To a pressure vessel was added 4-(3-bromopyridin-2-yloxy)aniline (7.23 g, 27.3 mmol) and 2-fluoro-5-methylpyridine (3.03 mL, 27.2 mmol) in NMP (13.61 mL) to stir at 170° C. Upon completion, the reaction mixture was diluted with water and extracted with EtOAc. The organic extract was washed with water, sat NaCl, dried with magnesium sulfate, filtered, and concentrated. The crude product was adsorbed onto a plug of silica gel and chromatographed to provide N-(4-(3-bromopyridin-2-yloxy)phenyl)-5-methylpyridin-2-amine.

Aufarbeitung

  1. extractionextracted with EtOAc
  2. extractionThe organic extract
  3. washwas washed with water
  4. dry with materialdried with magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customchromatographed

Quellen und Nachweise

ORD-Eintrag
ord-9885f166e218438e8b457acebbf4f82e
Quelldatensatz
uspto-grants-2014_01
Patentnummer
US08637500B2

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