Cesium carbonate → HCID 131724882, compound

HRID 2181575Notes

Reaction equation

HRID 2181575 reaction equation
[ClH:1].[OH:2][NH:3][C:4]([C:6]1([S:15]([C:18]2[CH:23]=[CH:22][C:21](SC3C=CC=CC=3)=[CH:20][CH:19]=2)(=[O:17])=[O:16])[CH2:11][CH2:10][N:9](CC#C)[CH2:8][CH2:7]1)=[O:5].C(=O)([O-])[O-:32].[Cs+].[Cs+].[F:37][C:38]([F:48])([F:47])[O:39][C:40]1[CH:45]=[CH:44][C:43](O)=[CH:42][CH:41]=1>CN(C)C=O>[ClH:1].[OH:2][NH:3][C:4]([C:6]1([S:15]([C:18]2[CH:23]=[CH:22][C:21]([O:32][C:41]3[CH:42]=[CH:43][CH:44]=[CH:45][C:40]=3[O:39][C:38]([F:48])([F:47])[F:37])=[CH:20][CH:19]=2)(=[O:16])=[O:17])[CH2:11][CH2:10][NH:9][CH2:8][CH2:7]1)=[O:5]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 70015p-(Trifluoromethoxy)phenolHCID 9890734HCID 9890734, compound

Product 1

HCID 131724882HCID 131724882, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Part A: To a solution of the product of Example 9, Part D (1.5 g, 3.61 mmol) in N,N-dimethylformamide (10 mL) was added cesium carbonate (2.94 g, 9.03 mmol) and 4-(trifluoromethoxy)phenol (0.70 mL, 5.41 mmol). The solution was heated to ninety degrees Celsius for 20 hours. The solution was partitioned between ethyl acetate and H2O and the organic layer was washed with saturated NaCl and dried over Na2SO4. Filtration through a silica pad (ethyl acetate) provided the phenoxyphenol as a yellow oil (2.11 g, quantitative yield). MS (CI) MNa+ calculated for C26H30NO8SF3: 596, found 596.

Workup

  1. temperatureThe solution was heated to ninety degrees Celsius for 20 hours
  2. customThe solution was partitioned between ethyl acetate and H2O
  3. washthe organic layer was washed with saturated NaCl
  4. dry with materialdried over Na2SO4
  5. filtrationFiltration through a silica pad (ethyl acetate)

Sources & evidence

ORD record
ord-414803d00e0a443682ec94d037c56e70
Source dataset
uspto-grants-2005_05
Patent number
US06890937B2

Reaction notes

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