Cesium carbonate → HCID 22285186, compound

HRID 2099852Notes

Reaction equation

HRID 2099852 reaction equation
O1CCOCC1.[CH3:7][O:8][C:9]1[CH:14]=[CH:13][C:12](OB(O)O)=[CH:11][CH:10]=1.C(=O)([O-])[O-].[Cs+].[Cs+].Cl[C:26]1[CH:27]=[CH:28][C:29]([N+:33]([O-:35])=[O:34])=[C:30]([CH:32]=1)[NH2:31]>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].C(P(C(C)(C)C)C(C)(C)C)(C)(C)C.C(Cl)(Cl)Cl.C(OCC)C>[CH3:7][O:8][C:9]1[CH:14]=[CH:13][C:12]([C:26]2[CH:27]=[CH:28][C:29]([N+:33]([O-:35])=[O:34])=[C:30]([CH:32]=2)[NH2:31])=[CH:11][CH:10]=1

Participants

9

Reactant 4

HCID 10796Cesium carbonateHCID 312751,4-Dioxane2×HCID 742185-Chloro-2-nitroanilineHCID 147699944-Methoxyphenyl boric acid

Product 1

HCID 22285186HCID 22285186, compoundYield 102.4%

Reagents, catalysts & solvents 4

HCID 83681Tris(1,1-dimethylethyl)phosphineCatalystHCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 3283Diethyl EtherSolventHCID 6212ChloroformSolvent

Conditions

Temperature
85 °C

Procedure

Under an argon stream, a dioxane solution (10 ml) of tris-t-butylphosphine (240 mg) was added to a mixture of p-methoxyphenyl boric acid (4.364 g), tris(dibenzylideneacetone)dipalladium (452 mg), cesium carbonate (10.561 g), 5-chloro-2-nitroaniline (4505 mg) and dioxane (50 ml), followed by 2 hours and 10 minutes of heating at 85° C. After cooling to room temperature on standing, diethyl ether (500 ml) and chloroform (500 ml) were added thereto. After insoluble matter was removed by filtration, the filtrate was concentrated to obtain an aimed compound, 5-(4′-methoxyphenyl)-2-nitroaniline (6.5 g).

Workup

  1. additionwere added
  2. customAfter insoluble matter was removed by filtration
  3. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-9b261649b8a5428fad261ebdf945df32
Source dataset
uspto-grants-2009_08
Patent number
US07569688B2

Reaction notes

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