3-Chlorophenol → HCID 67958151, Verbindung

HRID 72482

Reaktionsgleichung

Reaktionsgleichung von HRID 72482
[Cl:1][C:2]1[CH:3]=[C:4]([OH:8])[CH:5]=[CH:6][CH:7]=1.C(=O)([O-])[O-].[K+].[K+].[F:15][C:16]1[CH:17]=[N:18][C:19]([N:26]2[CH2:29][CH:28](OS(C)(=O)=O)[CH2:27]2)=[C:20]([CH:25]=1)[C:21]([O:23]C)=[O:22].[OH-].[Na+]>CN(C)C=O>[Cl:1][C:2]1[CH:3]=[C:4]([CH:5]=[CH:6][CH:7]=1)[O:8][CH:28]1[CH2:29][N:26]([C:19]2[N:18]=[CH:17][C:16]([F:15])=[CH:25][C:20]=2[C:21]([OH:23])=[O:22])[CH2:27]1

Komponenten

6

Edukt 4

HCID 79333-ChlorophenolHCID 11430Potassium CarbonateHCID 14798Sodium HydroxideHCID 86697878Methyl 5-fluoro-2-(3-((methylsulfonyl)oxy)azetidin-1-yl)nicotinate

Produkt 1

HCID 67958151HCID 67958151, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
160 °C

Versuchsvorschrift

To a solution of 3-chlorophenol (0.035 ml, 0.328 mmol) in dimethylformamide (1 ml), potassium carbonate (45.42 mg, 0.328 mmol) and the reaction mixture was stirred 2 h at 80° C. Methyl 5-fluoro-2-(3-((methylsulfonyl)oxy)azetidin-1-yl)nicotinate (D71) (100 mg, 0.328 mmol) was added and the resulting reaction mixture was heated 12 h at 160° C. After cooling at room temperature 1N NaOH (0.656 ml, 0.656 mmol) was added and the reaction mixture heated 2 h at 120° C. Solvents were evaporated in vacuo and the residue was loaded on SPE-SCX cartridge (5 g). Ammonia fractions after solvent evaporation afforded a residue that was further purified by Biotage column SNAP-C18 (30 g) eluting with water/acetic acid (0.1%)/acetonitrile-acetic acid (0.1%) from 70/30 to 0/100.

Aufarbeitung

  1. customthe resulting reaction mixture
  2. additionwas added
  3. temperaturethe reaction mixture heated 2 h at 120° C
  4. customSolvents were evaporated in vacuo
  5. customAmmonia fractions after solvent evaporation
  6. customafforded a residue that
  7. customwas further purified by Biotage column
  8. wash(30 g) eluting with water/acetic acid (0.1%)/acetonitrile-acetic acid (0.1%) from 70/30 to 0/100

Quellen und Nachweise

ORD-Eintrag
ord-96a034a9baf64bcea343537b99407cc2
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08828987B2

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