Sodium Carbonate → HCID 68962324, compound

HRID 2191651Notes

Reaction equation

HRID 2191651 reaction equation
Br[C:2]1[CH:14]=[CH:13][C:5]([C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7])=[C:4]([NH:15][C:16]2[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=2)[CH:3]=1.[Cl:23][C:24]1[CH:25]=[C:26](B(O)O)[CH:27]=[CH:28][CH:29]=1.C(=O)([O-])[O-].[Na+].[Na+]>CN(C)C(=O)C>[Cl:23][C:24]1[CH:29]=[C:28]([C:2]2[CH:14]=[CH:13][C:5]([C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7])=[C:4]([NH:15][C:16]3[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=3)[CH:3]=2)[CH:27]=[CH:26][CH:25]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 2734323(3-Chlorophenyl)boronic acidHCID 68956988Tert-butyl 4-bromo-2-(4-fluoroanilino)benzoate

Product 1

HCID 68962324HCID 68962324, compound

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Conditions

Temperature
110 °C

Procedure

To N,N-dimethylacetamide 2.5 mL solution of tert-butyl 4-bromo-2-(4-fluoroanilino)benzoate 80 mg were added 3-chlorophenylboronic acid 51 mg, sodium carbonate 58 mg and polymer-carried di(acetato)dicyclohexylphenylphosphine palladium(II) 7 mg, and it was stirred at 110° C. for 19 hours. After the reaction mixture was cooled to room temperature, polymer-carried di(acetato)dicyclohexylphenylphosphine palladium(II) 7 mg was added to it, and it was stirred at 110° C. for 30 hours. After the reaction mixture was cooled to room temperature, insoluble matter was filtrated, and 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 and saturated sodium chloride aqueous solution, 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=4:1] to give tert-butyl 4-(3-chlorophenyl)-2-(4-fluoroanilino)benzoate.

Workup

  1. temperatureAfter the reaction mixture was cooled to room temperature
  2. stirringwas stirred at 110° C. for 30 hours
  3. temperatureAfter the reaction mixture was cooled to room temperature
  4. filtrationinsoluble matter was filtrated
  5. additionethyl acetate and 10% citric acid aqueous solution were added to it
  6. customThe organic layer was separated
  7. washafter sequential washing with 10% citric acid aqueous solution and saturated sodium chloride aqueous solution
  8. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-fe33bb36901f4bc19e6641403f353d6d
Source dataset
uspto-grants-2012_12
Patent number
US08327467B2

Reaction notes

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