Cesium carbonate → HCID 59443036, compound

HRID 1959142Notes

Reaction equation

HRID 1959142 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:17]3[C:12](=[CH:13][C:14](OS(C(F)(F)F)(=O)=O)=[CH:15][CH:16]=3)[O:11][C:10]([CH3:27])([CH3:26])[CH:9]=2)=[CH:4][CH:3]=1.[C:28](=[O:35])([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])[NH2:29].C(=O)([O-])[O-].[Cs+].[Cs+]>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].O1CCOCC1>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[C:17]3[C:12](=[CH:13][C:14]([NH:29][C:28](=[O:35])[O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[CH:15][CH:16]=3)[O:11][C:10]([CH3:27])([CH3:26])[CH:9]=2)=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 77922tert-Butyl carbamateHCID 86676262HCID 86676262, compound

Product 1

HCID 59443036HCID 59443036, compound

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 312751,4-DioxaneSolvent

Procedure

A mixture of the compound obtained in (3) described above (5.9 g), tert-butyl carbamate (2.06 g), cesium carbonate (9.6 g), tris(dibenzylideneacetone)dipalladium(0) (420 mg), biphenyl-2-yl-dibutylphosphate (840 mg) and 1,4-dioxane (30 mL) was heated under reflux under nitrogen atmosphere for 10 hours. The reaction mixture was filtered, and the filtrate was concentrated in vacuo. The residue is purified by column chromatography on silica gel (Solvent; petroleum ether/ethyl acetate=100/1) to give the titled compound (2.8 g) as a yellow powder.

Workup

  1. additionA mixture of the compound
  2. temperaturewas heated
  3. temperatureunder reflux under nitrogen atmosphere for 10 hours
  4. filtrationThe reaction mixture was filtered
  5. concentrationthe filtrate was concentrated in vacuo
  6. customThe residue is purified by column chromatography on silica gel (Solvent; petroleum ether/ethyl acetate=100/1)

Sources & evidence

ORD record
ord-e2870ad9afae41fdaf885a0d1019fcce
Source dataset
uspto-grants-2013_04
Patent number
US08410166B2

Reaction notes

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