Sodium Carbonate → HCID 22142143, compound

HRID 1824697Notes

Reaction equation

HRID 1824697 reaction equation
Br[C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][C:3]=1[F:9].[F:10][C:11]([F:22])([F:21])[C:12]1[CH:13]=[C:14](B(O)O)[CH:15]=[CH:16][CH:17]=1.C(=O)([O-])[O-].[Na+].[Na+].C(P(C(C)(C)C)C1C=CC=CC=1C1C=CC=CC=1)(C)(C)C>C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[F:9][C:3]1[CH:4]=[C:5]([NH2:6])[CH:7]=[CH:8][C:2]=1[C:16]1[CH:15]=[CH:14][CH:13]=[C:12]([C:11]([F:22])([F:21])[F:10])[CH:17]=1

Participants

6

Reactant 4

HCID 10340Sodium CarbonateHCID 8218484-Bromo-3-fluoroanilineHCID 27342152-(Di-tert-butylphosphino)biphenylHCID 27343883-(Trifluoromethyl)phenylboronic acid

Product 1

HCID 22142143HCID 22142143, compoundYield 43.3%

Reagents, catalysts & solvents 1

HCID 167845palladium(II) acetateCatalyst

Conditions

Temperature
90 °C

Procedure

A mixture of 4-bromo-3-fluoroaniline (4.3 g), 3-trifluoromethylphenylboronic acid (4.4 g), sodium carbonate (6.5 g), palladium(II) acetate (0.22 g) and 2-(di-t-butylphosphino)biphenyl (0.60 g) were weighed into a reaction tube and flushed with nitrogen. A 70:30 mixture of dioxane/water (50 mL) was then added and the mixture was heated at 90° C. for 16 h. Ethyl acetate and water was added and the phases separated. The organic phase was dried and concentrated. The residue was purified by column chromatography on silica to give a solid (2.5 g).

Workup

  1. customwere weighed into a reaction tube
  2. customflushed with nitrogen
  3. additionA 70:30 mixture of dioxane/water (50 mL)
  4. additionwas then added
  5. additionEthyl acetate and water was added
  6. customthe phases separated
  7. customThe organic phase was dried
  8. concentrationconcentrated
  9. customThe residue was purified by column chromatography on silica

Sources & evidence

ORD record
ord-ec7b9322bb064420a52e85853a1acd62
Source dataset
uspto-grants-2006_05
Patent number
US07045512B2

Reaction notes

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