Potassium Carbonate → HCID 66773063, compound

HRID 1644881Notes

Reaction equation

HRID 1644881 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[C:12]([C:13]2[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][CH:14]=2)=[C:11]([O:20][CH2:21][C:22]([OH:24])=[O:23])[C:10]([C:25](=[O:39])[NH:26][C@@H:27]([C:29]2[CH:34]=[CH:33][C:32]([C:35]([F:38])([F:37])[F:36])=[CH:31][CH:30]=2)[CH3:28])=[N:9]1.C(=O)([O-])[O-].[K+].[K+].Br[CH:47](C)[C:48](OCC)=O>CC(C)=O>[CH2:47]([O:23][C:22](=[O:24])[CH2:21][O:20][C:11]1[C:10]([C:25](=[O:39])[NH:26][C@@H:27]([C:29]2[CH:30]=[CH:31][C:32]([C:35]([F:38])([F:36])[F:37])=[CH:33][CH:34]=2)[CH3:28])=[N:9][N:8]([C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[Cl:1])[C:12]=1[C:13]1[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][CH:14]=1)[CH3:48]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 79040Ethyl 2-bromopropionateHCID 59146317HCID 59146317, compound

Product 1

HCID 66773063HCID 66773063, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of [E1] (156 mg, 0.28 mmol) in acetone was added potassium carbonate (26 mg) and ethyl 2-bromopropionate (11.7 ul, 0.10 mmol). The resulting suspension was stirred overnight at room temperature then partitioned between dichloromethane and brine. The organic phase was dried over anhydrous magnesium sulphate, filtered and evaporated in vacuo. The residue was purified by column chromatography over silica (2 g) silica, eluting with dichloromethane then ethyl acetate/heptane (1/1) to give 142 mg of {1-(2-Chloro-phenyl)-5-(4-chloro-phenyl)-3-[(R)-1-(4-trifluoromethyl-phenyl)-ethylcarbamoyl]-1H-pyrazol-4-yloxy}-acetic acid ethyl ester

Workup

  1. customthen partitioned between dichloromethane and brine
  2. dry with materialThe organic phase was dried over anhydrous magnesium sulphate
  3. filtrationfiltered
  4. customevaporated in vacuo
  5. customThe residue was purified by column chromatography over silica (2 g) silica
  6. washeluting with dichloromethane

Sources & evidence

ORD record
ord-5c8e31ddd6e6473da8c54aca52463aec
Source dataset
uspto-grants-2012_02
Patent number
US08124634B2

Reaction notes

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