Cesium carbonate → HCID 86645884, compound

HRID 2386888Notes

Reaction equation

HRID 2386888 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([OH:8])[CH:5]=[CH:4][C:3]=1[CH:9]([CH3:28])[C:10]([C:16]1[CH:17]=[CH:18][C:19]2[O:24][CH2:23][C:22](=[O:25])[N:21]([CH3:26])[C:20]=2[CH:27]=1)([OH:15])[C:11]([F:14])([F:13])[F:12].F[C:30]1[CH:37]=[CH:36][C:33]([CH:34]=[O:35])=[C:32]([C:38]([F:41])([F:40])[F:39])[CH:31]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>>[Cl:1][C:2]1[CH:7]=[C:6]([CH:5]=[CH:4][C:3]=1[CH:9]([CH3:28])[C:10]([OH:15])([C:16]1[CH:17]=[CH:18][C:19]2[O:24][CH2:23][C:22](=[O:25])[N:21]([CH3:26])[C:20]=2[CH:27]=1)[C:11]([F:12])([F:13])[F:14])[O:8][C:30]1[CH:37]=[CH:36][C:33]([CH:34]=[O:35])=[C:32]([C:38]([F:39])([F:41])[F:40])[CH:31]=1

Participants

4

Reactant 3

HCID 10796Cesium carbonateHCID 5229404-Fluoro-2-(trifluoromethyl)benzaldehydeHCID 666972396-[(2-chloro-4-hydroxy-phenyl)-1-hydroxy-1-trifluoromethyl-propyl]-4-methyl-4H-benzo[1,4]oxazin-3-one

Product 1

HCID 86645884HCID 86645884, compoundYield 64.5%

Procedure

To a solution of 6-[2-(2-chloro-4-hydroxy-phenyl)-1-hydroxy-1-trifluoromethyl-propyl]-4-methyl-4H-benzo[1,4]oxazin-3-one (100 mg, 0.24 mmol, Example 56, step 4) in N′N-dimethylacetamide (1.5 ml) were added 4-fluoro-2-(trifluoromethyl)benzaldehyde (69 mg, 0.36 mmol) and cesium carbonate (234 mg, 0.72 mmol). The mixture was stirred for 17 h at room temperature. Ice water was added and the mixture was extracted with AcOEt. The organic phase was washed with water, dried (MgSO4) and concentrated. The product was purified by column chromatography (silica gel, heptane/AcOEt 3:1) to give the title compound (91 mg) as white foam. MS (m/e, ISP neg. ion)=586.2 [M−H+].

Workup

  1. extractionthe mixture was extracted with AcOEt
  2. washThe organic phase was washed with water
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated
  5. customThe product was purified by column chromatography (silica gel, heptane/AcOEt 3:1)

Sources & evidence

ORD record
ord-f990b474d148459c8c2acad31450e6ca
Source dataset
uspto-grants-2012_09
Patent number
US08268820B2

Reaction notes

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