Potassium Carbonate → Tert-butyl 2-(4-(4-((2,4-dichlorophenethyl)carbamoyl)-3-fluorophenoxy)-3-cyanophenyl)acetate

HRID 1927788Notes

Reaction equation

HRID 1927788 reaction equation
[Cl:1][C:2]1[CH:20]=[C:19]([Cl:21])[CH:18]=[CH:17][C:3]=1[CH2:4][CH2:5][NH:6][C:7](=[O:16])[C:8]1[CH:13]=[CH:12][C:11]([OH:14])=[CH:10][C:9]=1[F:15].[C:22]([C:24]1[CH:25]=[C:26]([CH2:31][C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])[CH:27]=[CH:28][C:29]=1F)#[N:23].C([O-])([O-])=O.[K+].[K+]>CS(C)=O.O.C(OCC)(=O)C>[Cl:1][C:2]1[CH:20]=[C:19]([Cl:21])[CH:18]=[CH:17][C:3]=1[CH2:4][CH2:5][NH:6][C:7]([C:8]1[CH:13]=[CH:12][C:11]([O:14][C:29]2[CH:28]=[CH:27][C:26]([CH2:31][C:32]([O:34][C:35]([CH3:36])([CH3:38])[CH3:37])=[O:33])=[CH:25][C:24]=2[C:22]#[N:23])=[CH:10][C:9]=1[F:15])=[O:16]

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 45925946Tert-butyl 2-(3-cyano-4-fluorophenyl)acetateHCID 68467622N-(2,4-dichlorophenethyl)-2-fluoro-4-hydroxybenzamide

Product 1

HCID 68468374Tert-butyl 2-(4-(4-((2,4-dichlorophenethyl)carbamoyl)-3-fluorophenoxy)-3-cyanophenyl)acetateYield 2.3%

Reagents, catalysts & solvents 3

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
70 °C

Procedure

To a stirred solution of N-(2,4-dichlorophenethyl)-2-fluoro-4-hydroxybenzamide (420 mg, 1.28 mmol) and tert-butyl 2-(3-cyano-4-fluorophenyl)acetate (361 mg, 1.54 mmol) in DMSO (6 ml) was added K2CO3 (265 mg, 1.92 mmol). The reaction was heated stirred at 70° C. for one hour. The reaction was then stirred at 90° C. overnight. The reaction was diluted with water and ethyl acetate. The aqueous phase was extracted with ethyl acetate and the combined organic layers were washed with 10% Na2CO3 and brine, dried over MgSO4, filtered and concentrated. The crude product was purified by silica gel chromatography to give tert-butyl 2-(4-(4-((2,4-dichlorophenethyl)carbamoyl)-3-fluorophenoxy)-3-cyanophenyl)acetate (0.0157 g).

Workup

  1. temperatureThe reaction was heated
  2. stirringThe reaction was then stirred at 90° C. overnight
  3. extractionThe aqueous phase was extracted with ethyl acetate
  4. washthe combined organic layers were washed with 10% Na2CO3 and brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe crude product was purified by silica gel chromatography

Sources & evidence

ORD record
ord-a831125cfa3e42eda993adbe0bff688c
Source dataset
uspto-grants-2012_05
Patent number
US08183289B2

Reaction notes

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