2-(Tributylstannyl)pyridine → HCID 86691906, compound

HRID 2172873Notes

Reaction equation

HRID 2172873 reaction equation
[Cl:1][C:2]1[C:3](I)=[N:4][C:5]([Cl:8])=[CH:6][CH:7]=1.C([Sn](CCCC)(CCCC)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][N:16]=1)CCC>C1(C)C=CC=CC=1>[Cl:1][C:2]1[C:3]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][N:16]=2)=[N:4][C:5]([Cl:8])=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 6077842-(Tributylstannyl)pyridineHCID 84220500HCID 84220500, compound

Product 1

HCID 86691906HCID 86691906, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

The mixture of 3,6-dichloro-2-iodopyridine (21 g, 77% purity, 58.8 mmol), 2-(tributylstannyl)pyridine (37 g, 80% purity, 80 mmol) in toluene (300 mL) was degassed, then Pd(PPh3)4 (730 mg) was added, the mixture was degassed again and stirred at reflux under N2 overnight. The mixture was concentrated and the residue was purified via silica gel column (petroleum ether:EtOAc=10:1˜5:1) to give title compound (10 g, 76%) as a gray solid.

Workup

  1. customwas degassed
  2. additionPd(PPh3)4 (730 mg) was added
  3. customthe mixture was degassed again
  4. temperatureat reflux under N2 overnight
  5. concentrationThe mixture was concentrated
  6. customthe residue was purified via silica gel column (petroleum ether:EtOAc=10:1˜5:1)

Sources & evidence

ORD record
ord-d1545b5988a742bc978b60401beb13d4
Source dataset
uspto-grants-2015_06
Patent number
US09056865B2

Reaction notes

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