Citric Acid → HCID 68962144, compound

HRID 2191729Notes

Reaction equation

HRID 2191729 reaction equation
Br[C:2]1[CH:6]=[CH:5][S:4][CH:3]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[F:13][C:14]1[CH:35]=[CH:34][C:17]([NH:18][C:19]2[CH:31]=[C:30]([CH:32]=[CH2:33])[CH:29]=[CH:28][C:20]=2[C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])=[CH:16][CH:15]=1.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C(OCC)(=O)C.CN(C)C(=O)C>[F:13][C:14]1[CH:35]=[CH:34][C:17]([NH:18][C:19]2[CH:31]=[C:30](/[CH:32]=[CH:33]/[C:2]3[CH:6]=[CH:5][S:4][CH:3]=3)[CH:29]=[CH:28][C:20]=2[C:21]([O:23][C:24]([CH3:27])([CH3:25])[CH3:26])=[O:22])=[CH:16][CH:15]=1

Participants

8

Reactant 4

HCID 311Citric AcidHCID 10796Cesium carbonateHCID 133833-BromothiopheneHCID 68959213Tert-butyl 2-(4-fluoroanilino)-4-vinylbenzoate

Product 1

HCID 68962144HCID 68962144, compound

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 8857Ethyl AcetateSolventHCID 31374DimethylacetamideSolvent

Conditions

Temperature
120 °C

Procedure

3-Bromothiophene 90 μL, cesium carbonate 0.31 g and palladium acetate 11 mg were added to N,N-dimethylacetamide 3.0 mL solution of tert-butyl 2-(4-fluoroanilino)-4-vinylbenzoate 0.15 g at room temperature, and it was stirred at 120° C. for 24 hours. After the reaction mixture was cooled to room temperature, ethyl acetate and 10% citric acid aqueous solution were added to it. The organic layer was separated and collected,dried over anhydrous magnesium sulfate after sequential washing with 10% citric acid aqueous solution, saturated sodium thiosulfate aqueous solution and saturated sodium chloride aqueous solution, and the solvent was removed under reduced pressure. The obtained residue was refined by silica gel column chromatography [Trikonex company, Flash Tube 2008, eluent; hexane:ethyl acetate=10:1] to give tert-butyl 2-(4-fluoroanilino)-4-((E)-2-(thiophen-3-yl)vinyl)benzoate.

Workup

  1. temperatureAfter the reaction mixture was cooled to room temperature
  2. customThe organic layer was separated
  3. washafter sequential washing with 10% citric acid aqueous solution, saturated sodium thiosulfate aqueous solution and saturated sodium chloride aqueous solution
  4. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-2698c94e0b714450b76a0fb407b7cc12
Source dataset
uspto-grants-2012_12
Patent number
US08327467B2

Reaction notes

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