Potassium Carbonate → Ethyl (4-{[(6-chloro-3-{[(3-chlorophenyl)methyl]oxy}-2-fluorophenyl)carbonyl]amino}phenyl)acetate

HRID 1879122Notes

Reaction equation

HRID 1879122 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH2:5]Br.[Cl:10][C:11]1[C:16]([C:17]([NH:19][C:20]2[CH:25]=[CH:24][C:23]([CH2:26][C:27]([O:29][CH2:30][CH3:31])=[O:28])=[CH:22][CH:21]=2)=[O:18])=[C:15]([F:32])[C:14]([OH:33])=[CH:13][CH:12]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[Cl:10][C:11]1[C:16]([C:17]([NH:19][C:20]2[CH:21]=[CH:22][C:23]([CH2:26][C:27]([O:29][CH2:30][CH3:31])=[O:28])=[CH:24][CH:25]=2)=[O:18])=[C:15]([F:32])[C:14]([O:33][CH2:5][C:4]2[CH:7]=[CH:8][CH:9]=[C:2]([Cl:1])[CH:3]=2)=[CH:13][CH:12]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 698381-(Bromomethyl)-3-chlorobenzeneHCID 59163346Ethyl (4-{[(6-chloro-2-fluoro-3-hydroxyphenyl)carbonyl]amino}phenyl)acetate

Product 1

HCID 59163349Ethyl (4-{[(6-chloro-3-{[(3-chlorophenyl)methyl]oxy}-2-fluorophenyl)carbonyl]amino}phenyl)acetateYield 84%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3-Chlorobenzylbromide (28 μl, 0.24 mmol) was added to a suspension of ethyl (4-{[(6-chloro-2-fluoro-3-hydroxyphenyl)carbonyl]amino}phenyl)acetate (80 mg, 0.228 mmol) and potassium carbonate (38 mg, 0.273 mmol) in dimethylformamide (3 ml) and the reaction was stirred at room temperature for 4 hrs. The solvent was evaporated and the residue partitioned between water and ethyl acetate. The organic layer was separated, dried (Na2SO4) and the solvent evaporated to afford the title compound as a colourless oil (91 mg, 84%).

Workup

  1. customThe solvent was evaporated
  2. customthe residue partitioned between water and ethyl acetate
  3. customThe organic layer was separated
  4. dry with materialdried (Na2SO4)
  5. customthe solvent evaporated

Sources & evidence

ORD record
ord-779175e7488842cea6f093149d9b45c7
Source dataset
uspto-grants-2012_11
Patent number
US08314147B2

Reaction notes

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