Potassium Carbonate → HCID 68467168, compound

HRID 453486Notes

Reaction equation

HRID 453486 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([CH2:10][C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH:6]=[CH:7][C:8]=1F)#[N:2].[Cl:18][C:19]1[CH:20]=[C:21]([CH:32]=[CH:33][C:34]=1[Cl:35])[C:22]([NH:24][C:25]1[CH:30]=[CH:29][C:28]([OH:31])=[CH:27][CH:26]=1)=[O:23].C(=O)([O-])[O-].[K+].[K+]>CS(C)=O.C(OCC)(=O)C.C(=O)([O-])[O-].[Na+].[Na+]>[C:1]([C:3]1[CH:4]=[C:5]([CH2:10][C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH:6]=[CH:7][C:8]=1[O:31][C:28]1[CH:29]=[CH:30][C:25]([NH:24][C:22](=[O:23])[C:21]2[CH:32]=[CH:33][C:34]([Cl:35])=[C:19]([Cl:18])[CH:20]=2)=[CH:26][CH:27]=1)#[N:2]

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 9768083,4-dichloro-N-(4-hydroxyphenyl)benzamideHCID 45925946Tert-butyl 2-(3-cyano-4-fluorophenyl)acetate

Product 1

HCID 68467168HCID 68467168, compoundYield 59.1%

Reagents, catalysts & solvents 3

HCID 679Dimethyl SulfoxideSolventHCID 8857Ethyl AcetateSolventHCID 10340Sodium CarbonateSolvent

Conditions

Temperature
125 °C

Procedure

tert-Butyl 2-(3-cyano-4-fluorophenyl)acetate (2.0 g, 8.5 mmol) and the product of step A (2.9 g, 10 mmol) were diluted with DMSO (22 mL) followed by the addition of potassium carbonate (1.4 g, 10 mmol). The reaction was heated to 125° C. and stirred for 12 hours. The reaction mixture was then cooled to room temperature, diluted with ethyl acetate and 10% aqueous sodium carbonate. The layers were separated and the organic layer was washed with 10% aqueous sodium carbonate two more times followed by water and brine. The organic material was dried over MgSO4, filtered and concentrated. The material was purified using a biotage 40M column eluting with hexanes:ethyl acetate (8:2) to yield tert-butyl 2-(3-cyano-4-(4-(3,4-dichlorobenzamido)phenoxy)phenyl)acetate (2.5 g, 59% yield) as a white solid.

Workup

  1. temperatureThe reaction mixture was then cooled to room temperature
  2. customThe layers were separated
  3. washthe organic layer was washed with 10% aqueous sodium carbonate two more times
  4. dry with materialThe organic material was dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe material was purified
  8. washeluting with hexanes:ethyl acetate (8:2)

Sources & evidence

ORD record
ord-423ae94088af42e1be130c1b84711519
Source dataset
uspto-grants-2013_07
Patent number
US08492437B2

Reaction notes

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