Cesium carbonate → N-[4-(4-Trifluoromethoxy-phenoxy)-phenyl]-methanesulfonamide

HRID 1716301

Reaktionsgleichung

Reaktionsgleichung von HRID 1716301
[F:1][C:2]([F:12])([F:11])[O:3][C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][CH:5]=1.C([O-])([O-])=O.[Cs+].[Cs+].I[C:20]1[CH:25]=[CH:24][C:23]([NH:26][S:27]([CH3:30])(=[O:29])=[O:28])=[CH:22][CH:21]=1.CC(C)(C(=O)CC(=O)C(C)(C)C)C>CN1C(=O)CCC1.Cl[Cu]>[F:1][C:2]([F:11])([F:12])[O:3][C:4]1[CH:5]=[CH:6][C:7]([O:10][C:20]2[CH:21]=[CH:22][C:23]([NH:26][S:27]([CH3:30])(=[O:28])=[O:29])=[CH:24][CH:25]=2)=[CH:8][CH:9]=1

Komponenten

7

Edukt 4

HCID 10796Cesium carbonateHCID 70015p-(Trifluoromethoxy)phenolHCID 707002,2,6,6-Tetramethyl-3,5-heptanedioneHCID 836147N-(4-iodophenyl)methanesulfonamide

Produkt 1

HCID 68514657N-[4-(4-Trifluoromethoxy-phenoxy)-phenyl]-methanesulfonamide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 62652Cuprous chlorideKatalysatorHCID 13387N-methyl-2-pyrrolidoneLösungsmittel

Reaktionsbedingungen

Temperatur
110 °C

Versuchsvorschrift

To a solution of 4-trifluoromethoxy-phenol (0.7 mL, 5.4 mmol) in NMP (6 mL) was added Cs2CO3 (1.76 g, 5.4 mmol). The slurry was degassed for 2 min and added N-(4-iodo-phenyl)-methanesulfonamide (0.80 g, 2.7 mmol) from Example 33, Step A, 2,2,6,6-tetramethylheptane-3,5-dione (0.056 mL, 0.27 mmol) and CuCl (0.134 g, 1.35 mmol) subsequently. The reaction mixture was heated to 110° C. under N2 overnight. The reaction was brought to the usual work-up and the crude material was purified by chromatography (20% EtOAc/hexanes). MS (EI) 348 (M+H)+.

Aufarbeitung

  1. customThe slurry was degassed for 2 min
  2. customthe crude material was purified by chromatography (20% EtOAc/hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-35ebee4bc113423f9af397a238b60cdc
Quelldatensatz
uspto-grants-2010_09
Patentnummer
US07803793B2

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