Sodium hydride → Tert-butyl 2-fluoro-4-(2-(methylamino)-3-nitropyridin-4-yloxy)phenylcarbamate

HRID 2272684

Reaktionsgleichung

Reaktionsgleichung von HRID 2272684
[F:1][C:2]1[CH:7]=[C:6]([OH:8])[CH:5]=[CH:4][C:3]=1[NH:9][C:10](=[O:16])[O:11][C:12]([CH3:15])([CH3:14])[CH3:13].[H-].[Na+].Cl[C:20]1[CH:25]=[CH:24][N:23]=[C:22]([NH:26][CH3:27])[C:21]=1[N+:28]([O-:30])=[O:29]>CS(C)=O>[F:1][C:2]1[CH:7]=[C:6]([O:8][C:20]2[CH:25]=[CH:24][N:23]=[C:22]([NH:26][CH3:27])[C:21]=2[N+:28]([O-:30])=[O:29])[CH:5]=[CH:4][C:3]=1[NH:9][C:10](=[O:16])[O:11][C:12]([CH3:13])([CH3:15])[CH3:14]

Komponenten

5

Edukt 3

HCID 24758Sodium hydrideHCID 249031234-Chloro-N-methyl-3-nitropyridin-2-amineHCID 441857034-(Boc-amino)-3-fluoro-phenol

Produkt 1

HCID 57507628Tert-butyl 2-fluoro-4-(2-(methylamino)-3-nitropyridin-4-yloxy)phenylcarbamate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 679Dimethyl SulfoxideLösungsmittel2×

Versuchsvorschrift

Tert-butyl 2-fluoro-4-hydroxyphenylcarbamate (3.25 g, 14.4 mmol) was dissolved in DMSO (25 mL) and the solution was stirred under an argon atmosphere for 20 minutes. Sodium hydride (60% in mineral oil, 580 mg, 14.4 mmol) was added portionwise and the dark solution was stirred at room temperature for 1 hour. 4-chloro-N-methyl-3-nitropyridin-2-amine (2.7 g, 14.4 mmol) dissolved in DMSO (5 mL) was added at once and the red solution was stirred at 50° C. for 2 hours. The solution was cooled, poured onto crushed ice (200 g) and extracted with ethyl acetate (3×100 mL). The organic phases were washed with brine, dried and evaporated to give the title compound as a yellow solid.

Aufarbeitung

  1. stirringthe dark solution was stirred at room temperature for 1 hour
  2. additionwas added at once and the red solution
  3. stirringwas stirred at 50° C. for 2 hours
  4. temperatureThe solution was cooled
  5. additionpoured
  6. extractionextracted with ethyl acetate (3×100 mL)
  7. washThe organic phases were washed with brine
  8. customdried
  9. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-fc5ab00c152d4b898fbf06988167055f
Quelldatensatz
uspto-grants-2015_09
Patentnummer
US09120789B2

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