Sodium Carbonate → HCID 68958883, compound

HRID 2191653Notes

Reaction equation

HRID 2191653 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.[CH3:23][O:24][C:25]1[CH:30]=[CH:29][C:28](B(O)O)=[CH:27][N:26]=1.C(=O)([O-])[O-].[Na+].[Na+]>CN(C)C(=O)C>[F:22][C:19]1[CH:20]=[CH:21][C:16]([NH:15][C:4]2[CH:3]=[C:2]([C:28]3[CH:29]=[CH:30][C:25]([O:24][CH3:23])=[N:26][CH:27]=3)[CH:14]=[CH:13][C:5]=2[C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7])=[CH:17][CH:18]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 2734368(6-Methoxypyridin-3-yl)boronic acidHCID 68956988Tert-butyl 4-bromo-2-(4-fluoroanilino)benzoate

Product 1

HCID 68958883HCID 68958883, 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 0.10 g were added 2-methoxy-5-pyridinboronic acid 63 mg, sodium carbonate 72 mg and polymer-carried di(acetato)dicyclohexylphenylphosphine palladium(II) 8 mg, and it was stirred at 110° C. for 15 hours. After the reaction mixture was cooled to room temperature,2-methoxy-5-pyridinboronic acid 21 mg and polymer-carried di(acetato)dicyclohexylphenylphosphine palladium(II) 8 mg were added to it, and it was stirred at 110° C. for 36 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, 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=4:1] to give tert-butyl 2-(4-fluoroanilino)-4-(2-methoxypyridin-5-yl)benzoate.

Workup

  1. additionwere added to it, and it
  2. stirringwas stirred at 110° C. for 36 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. customcollected
  8. dry with materialdried over anhydrous magnesium sulfate
  9. washafter sequential washing with 10% citric acid aqueous solution and saturated sodium chloride aqueous solution
  10. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-a5bf22373e5f40ef89b58128a94c6301
Source dataset
uspto-grants-2012_12
Patent number
US08327467B2

Reaction notes

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