Potassium Carbonate → N-(sec-butylsulfonyl)-4-[(5-chloro-6-methoxypyridin-3-yl)oxy]-2,5-difluorobenzamide
Reaktionsgleichung
C(=O)([O-])[O-].[K+].[K+].[CH:7]([S:11]([NH:14][C:15](=[O:25])[C:16]1[CH:21]=[C:20]([F:22])[C:19](F)=[CH:18][C:17]=1[F:24])(=[O:13])=[O:12])([CH2:9][CH3:10])[CH3:8].[Cl:26][C:27]1[CH:28]=[C:29]([OH:35])[CH:30]=[N:31][C:32]=1[O:33][CH3:34]>CS(C)=O.O>[CH:7]([S:11]([NH:14][C:15](=[O:25])[C:16]1[CH:21]=[C:20]([F:22])[C:19]([O:35][C:29]2[CH:30]=[N:31][C:32]([O:33][CH3:34])=[C:27]([Cl:26])[CH:28]=2)=[CH:18][C:17]=1[F:24])(=[O:13])=[O:12])([CH2:9][CH3:10])[CH3:8]Komponenten
6
Edukt 3
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 2
Reaktionsbedingungen
- Temperatur
- 90 °C
Versuchsvorschrift
Potassium carbonate (0.140 g, 1.01 mmol) was added to a stirred solution of N-(sec-butylsulfonyl)-2,4,5-trifluorobenzamide (Preparation 68, 0.090 g, 0.30 mmol) in DMSO (1 mL). After 10 minutes a solution of 5-chloro-6-methoxypyridin-3-ol (Preparation 77, 0.088 g, 0.51 mmol) in DMSO (2 mL) was added at room temperature. The mixture was heated at 90° C. for 72 hours. The reaction mixture was diluted with water (25 mL) and extracted with EtOAc (3×25 mL). The combined organics were washed with water (25 mL), dried over magnesium sulfate, filtered, evaporated in vacuo. The resulting crude product was purified by silica gel chromatography eluting with 0 to 66% EtOAc in heptane to yield the title compound (0.068 g):
Aufarbeitung
- extractionextracted with EtOAc (3×25 mL)
- washThe combined organics were washed with water (25 mL)
- dry with materialdried over magnesium sulfate
- filtrationfiltered
- customevaporated in vacuo
- customThe resulting crude product was purified by silica gel chromatography
- washeluting with 0 to 66% EtOAc in heptane
Quellen und Nachweise
- ORD-Eintrag
- ord-86492491a40b49ce90fd01bffc4fd302
- Quelldatensatz
- uspto-grants-2013_11
- Patentnummer
- US08592629B2
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