Cesium carbonate → HCID 59443036, compound

HRID 2380907Notes

Reaction equation

HRID 2380907 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-c4c332460c67499d84775f00a987b0d2
Source dataset
uspto-grants-2012_09
Patent number
US08258131B2

Reaction notes

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