Sodium hydride → 4-(4-Amino-2,5-difluorophenoxy)pyridine-2-carboxamide

HRID 520672Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 520672
[NH2:1][C:2]1[C:7]([F:8])=[CH:6][C:5]([OH:9])=[C:4]([F:10])[CH:3]=1.Cl[C:12]1[CH:17]=[CH:16][N:15]=[C:14]([C:18]([NH2:20])=[O:19])[CH:13]=1.[H-].[Na+]>CN(C=O)C.O>[NH2:1][C:2]1[C:7]([F:8])=[CH:6][C:5]([O:9][C:12]2[CH:17]=[CH:16][N:15]=[C:14]([C:18]([NH2:20])=[O:19])[CH:13]=2)=[C:4]([F:10])[CH:3]=1

Komponenten

6

Edukt 3

HCID 24758Sodium hydrideHCID 3035434-Chloropyridine-2-carboxamideHCID 27787624-Amino-2,5-difluorophenol

Produkt 1

HCID 247886284-(4-Amino-2,5-difluorophenoxy)pyridine-2-carboxamideAusbeute 30,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a mixture of 4-amino-2,5-difluorophenol (100 mg, 0.64 mmol), and 4-chloropicolinamide (110 mg, 0.71 mmol) in DMF (2 mL) was added NaH (80 mg, 1.3 mmol, 60% dispersed in mineral oil). The reaction mixture was microwaved at 120° C. for 1.5 hours, then cooled to rt, diluted with water (20 mL), and extracted with EtOAc (30 mL×3). The combined organic phases were washed with brine (80 mL), dried over Na2SO4 and concentrated in vacuo. The residue was purified by flash column chromatography with (EtOAc/PE (v/v)=4/1) to afford the title compound as a brown solid (52 mg, 26%).

Aufarbeitung

  1. customThe reaction mixture was microwaved at 120° C. for 1.5 hours
  2. extractionextracted with EtOAc (30 mL×3)
  3. washThe combined organic phases were washed with brine (80 mL)
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by flash column chromatography with (EtOAc/PE (v/v)=4/1)

Quellen und Nachweise

ORD-Eintrag
ord-22856af2919440daad49437f93317de0
Quelldatensatz
uspto-grants-2016_05
Patentnummer
US09326975B2

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