Potassium Phosphate, Tribasic → 3-(4-(4-Chlorophenoxy)phenyl)-1-(4-methoxyphenyl)-4-(3-(trifluoromethyl)phenyl)-imidazolidin-2-one

HRID 1972229Notes

Reaction equation

HRID 1972229 reaction equation
[Cl:1][C:2]1[CH:30]=[CH:29][C:5]([O:6][C:7]2[CH:12]=[CH:11][C:10]([N:13]3[CH:17]([C:18]4[CH:23]=[CH:22][CH:21]=[C:20]([C:24]([F:27])([F:26])[F:25])[CH:19]=4)[CH2:16][NH:15][C:14]3=[O:28])=[CH:9][CH:8]=2)=[CH:4][CH:3]=1.I[C:32]1[CH:37]=[CH:36][C:35]([O:38][CH3:39])=[CH:34][CH:33]=1.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>[Cu]I>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:6][C:7]2[CH:8]=[CH:9][C:10]([N:13]3[CH:17]([C:18]4[CH:23]=[CH:22][CH:21]=[C:20]([C:24]([F:26])([F:25])[F:27])[CH:19]=4)[CH2:16][N:15]([C:32]4[CH:37]=[CH:36][C:35]([O:38][CH3:39])=[CH:34][CH:33]=4)[C:14]3=[O:28])=[CH:11][CH:12]=2)=[CH:29][CH:30]=1

Participants

5

Reactant 3

HCID 62657Potassium Phosphate, TribasicHCID 696764-IodoanisoleHCID 594856551-(4-(4-Chlorophenoxy)phenyl)-5-(3-(trifluoromethyl)phenyl)imidazolidin-2-one

Product 1

HCID 594856823-(4-(4-Chlorophenoxy)phenyl)-1-(4-methoxyphenyl)-4-(3-(trifluoromethyl)phenyl)-imidazolidin-2-one

Reagents, catalysts & solvents 1

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)Catalyst

Conditions

Temperature
100 °C

Procedure

A reaction tube charged with 1-(4-(4-chlorophenoxy)phenyl)-5-(3-(trifluoromethyl)phenyl)imidazolidin-2-one (20.0 mg, 0.0462 mmol), 4-iodoanisole (13.0 mg, 0.0554 mmol), K3PO4 (19.6 mg, 0.0924 mmol), and catalytic amount of CuI is purged with nitrogen. 1,4-Dioxane (0.5 mL) and catalytic amount of trans-1,2-diaminocyclohexane are added via syringe. The reaction mixture is heated at 100° C. overnight, cooled down to room temperature, quenched with saturated NH4Cl aqueous solution (5 mL), and extracted with EtOAc (3×3 mL). The combined organic layer is concentrated and purified by preparatory LC/MS to provide the title compound; HPLC-MS calculated for C29H22ClF3N2O3 (M+H+) 539.1, found 539.1.

Workup

  1. customis purged with nitrogen
  2. addition1,4-Dioxane (0.5 mL) and catalytic amount of trans-1,2-diaminocyclohexane are added via syringe
  3. temperaturecooled down to room temperature
  4. customquenched with saturated NH4Cl aqueous solution (5 mL)
  5. extractionextracted with EtOAc (3×3 mL)
  6. concentrationThe combined organic layer is concentrated
  7. custompurified by preparatory LC/MS

Sources & evidence

ORD record
ord-462ac3723fc54b019a297fc39719a898
Source dataset
uspto-grants-2013_04
Patent number
US08431607B2

Reaction notes

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