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

HRID 1836182Notes

Reaction equation

HRID 1836182 reaction equation
[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]

Participants

7

Reactant 4

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

Product 1

HCID 219083066-[4-(2-Bromo-5-fluorophenyl)-2-hydroxy-4-methyl-2-trifluoromethylvaleroylamino]-4-methyl-2,3-benzoxazin-1-oneYield 68.7%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-45162ee3f41548798c0606ee302e3efc
Source dataset
uspto-grants-2004_08
Patent number
US06777409B2

Reaction notes

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