Cesium carbonate → 6-[4-(2-Bromo-5-fluorophenyl)-2-hydroxy-4-methyl-2-trifluoromethylvaleroylamino]-4-methyl-2,3-benzoxazin-1-one

HRID 1247562

Reaktionsgleichung

Reaktionsgleichung von HRID 1247562
[F:1][C:2]([Si](C)(C)C)([F:4])[F:3].C(=O)([O-])[O-].[Cs+].[Cs+].[Br:15][C:16]1[CH:21]=[CH:20][C:19]([F:22])=[CH:18][C:17]=1[C:23]([CH3:43])([CH3:42])[CH2:24][C:25](=[O:41])[C:26]([NH:28][C:29]1[CH:30]=[CH:31][C:32]2[C:37](=[O:38])[O:36][N:35]=[C:34]([CH3:39])[C:33]=2[CH:40]=1)=[O:27].[SiH4]>CN(C=O)C.C(OCC)(=O)C>[Br:15][C:16]1[CH:21]=[CH:20][C:19]([F:22])=[CH:18][C:17]=1[C:23]([CH3:43])([CH3:42])[CH2:24][C:25]([OH:41])([C:2]([F:4])([F:3])[F:1])[C:26]([NH:28][C:29]1[CH:30]=[CH:31][C:32]2[C:37](=[O:38])[O:36][N:35]=[C:34]([CH3:39])[C:33]=2[CH:40]=1)=[O:27]

Komponenten

7

Edukt 4

HCID 10796Cesium carbonateHCID 23953SilaneHCID 552549(Trifluoromethyl)trimethylsilaneHCID 21908380HCID 21908380, Verbindung

Produkt 1

HCID 219083066-[4-(2-Bromo-5-fluorophenyl)-2-hydroxy-4-methyl-2-trifluoromethylvaleroylamino]-4-methyl-2,3-benzoxazin-1-oneAusbeute 68,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

0.23 ml (1.25 mmol) of trifluoromethyl(trimethyl)silane and 256 mg (0.79 mmol) of cesium carbonate are added at 0° C. to a solution of 290 mg (0.63 mmol) of 6-[4-(2-bromo-5-fluorophenyl)-4-methyl-2-oxovaleroylamino]-4-methyl-2,3-benzoxazin-1-one in 7 ml of DMF. After 24 hours, the same amount of silane and base are added and stirred for another 24 hours at room temperature. The batch is diluted with 150 ml of ethyl acetate, washed with water and saturated NaCl, dried (Na2SO4) and concentrated by evaporation in a vacuum. Purification by column chromatography of the residue on silica gel yields 230 mg of product.

Aufarbeitung

  1. washwashed with water and saturated NaCl
  2. dry with materialdried (Na2SO4)
  3. concentrationconcentrated by evaporation in a vacuum
  4. customPurification by column chromatography of the residue on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-737c692587db4bb69c48ac5957d37f6c
Quelldatensatz
uspto-grants-2006_10
Patentnummer
US07129270B2

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