3-(Tributylstannyl)pyridine → palladium(II) acetate

HRID 1167984Notes

Reaction equation

HRID 1167984 reaction equation
ClC1C(I)=NSN=1.C([Sn](CCCC)(CCCC)C1C=NC=CC=1)CCC.C1C=CC(/C=C/[C:35](/[CH:37]=C/C2C=CC=CC=2)=[O:36])=CC=1.C1C=CC(/C=C/[C:53](/[CH:55]=C/C2C=CC=CC=2)=[O:54])=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=[O:72])=CC=1.[Pd:81].[Pd]>C1(C)C=CC=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.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[CH3:37][C:35]([O-:54])=[O:36].[CH3:55][C:53]([O-:72])=[O:54].[Pd+2:81]

Participants

6

Reactant 3

HCID 34838483-(Tributylstannyl)pyridineHCID 9811564Bis(dibenzylideneacetone)palladiumHCID 10214592HCID 10214592, compound

Product 1

HCID 167845palladium(II) acetateYield 76%

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 1140TolueneSolvent

Procedure

To a solution of 3-chloro-4-iodo-1,2,5-thiadiazole (62 mg, 0.25 mmol) in toluene (1 ml) under nitrogen is added tributyl-(3-pyridyl)stannane (92 mg, 0.25 mmol) and Pd2dba3 (5.7 mg, 5%mol). The resulting mixture is heated to reflux for 2 hours. A 76% yield was measured by quantitative HPLC, TLC (Hexane8/EtOAc2): only product. Similar results were obtained with 2% of Pd2(dba)3 as catalyst as well with Pd(CH3CN)2Cl2 or Pd(OAc)2.

Workup

  1. temperatureThe resulting mixture is heated
  2. temperatureto reflux for 2 hours
  3. customSimilar results

Sources & evidence

ORD record
ord-b23039d3e68045ae85b903fdb6961e2b
Source dataset
uspto-grants-2003_09
Patent number
US06620940B1

Reaction notes

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