Cesium carbonate → HCID 59442920, compound

HRID 2380905Notes

Reaction equation

HRID 2380905 reaction equation
[CH2:1]([C:3]1([CH2:29][CH3:30])[CH:12]=[C:11](OS(C(F)(F)F)(=O)=O)[C:10]2[C:5](=[CH:6][C:7]([O:21][Si](C(C)(C)C)(C)C)=[CH:8][CH:9]=2)[O:4]1)[CH3:2].[F:31][C:32]1[CH:37]=[CH:36][C:35](B(O)O)=[CH:34][CH:33]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>C(COC)OC.O.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[F:31][C:32]1[CH:37]=[CH:36][C:35]([C:11]2[C:10]3[C:5](=[CH:6][C:7]([OH:21])=[CH:8][CH:9]=3)[O:4][C:3]([CH2:1][CH3:2])([CH2:29][CH3:30])[CH:12]=2)=[CH:34][CH:33]=1

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 2856454-Fluorophenylboronic acidHCID 59442972HCID 59442972, compound

Product 1

HCID 59442920HCID 59442920, compound

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 18180031Water 1,2-dimethoxyethaneSolvent

Procedure

A mixture of the compound obtained in (3) described above (3.5 g), 4-fluorophenylboronic acid (1 g), cesium carbonate (12.7 g) and [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (350 mg, 10% wt) in dimethoxyethane/water (3/1; 60 mL) was heated under reflux under nitrogen atmosphere for 12 hours. The reaction solution was concentrated in vacuo, and the residue was extracted with ethyl acetate (40 ml×3). The combined organic layer was washed with saturated brine, dried over sodium sulfate, filtered and the filtrate was concentrated in vacuo. The residue is purified by column chromatography on silica gel (Solvent: petroleum ether/ethyl acetate=20/1) to give the titled compound (2 g) as a colorless powder.

Workup

  1. additionA mixture of the compound
  2. temperaturewas heated
  3. temperatureunder reflux under nitrogen atmosphere for 12 hours
  4. concentrationThe reaction solution was concentrated in vacuo
  5. extractionthe residue was extracted with ethyl acetate (40 ml×3)
  6. washThe combined organic layer was washed with saturated brine
  7. dry with materialdried over sodium sulfate
  8. filtrationfiltered
  9. concentrationthe filtrate was concentrated in vacuo
  10. customThe residue is purified by column chromatography on silica gel (Solvent: petroleum ether/ethyl acetate=20/1)

Sources & evidence

ORD record
ord-2eb20a5bd6584a40ab7f9f98aa1e50b7
Source dataset
uspto-grants-2012_09
Patent number
US08258131B2

Reaction notes

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