Allyltributylstannane → HCID 59633949, compound

HRID 1615077Notes

Reaction equation

HRID 1615077 reaction equation
Cl[C:2]1[CH:7]=[CH:6][N:5]=[C:4]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH:3]=1.[CH2:13]([Sn](CCCC)(CCCC)CCCC)[CH:14]=[CH2:15]>C1(C)C=CC=CC=1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH2:15]([C:2]1[CH:7]=[CH:6][N:5]=[C:4]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH:3]=1)[CH:14]=[CH2:13]

Participants

5

Reactant 2

HCID 90628AllyltributylstannaneHCID 130153594-Chloropyridine-2-carboxylic acid ethyl ester

Product 1

HCID 59633949HCID 59633949, compoundYield 73%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent

Conditions

Temperature
120 °C

Procedure

To a solution of ethyl 4-chloropyridin-2-carboxylate (0.37 g) and allyltributyltin (IV) (0.86 mL) in toluene (5.0 mL) was added tetrakis(triphenylphosphine)palladium (0) (0.12 g). The reaction mixture was stirred under nitrogen atmosphere at 120° C. for 12 hr. The solvent of the reaction mixture was removed under reduced pressure. The residue was purified by silica gel chromatography (Developing solvent: hexane/ethyl acetate=3/2) to give the title compound (0.28 g, 73%).

Workup

  1. customThe solvent of the reaction mixture was removed under reduced pressure
  2. customThe residue was purified by silica gel chromatography (Developing solvent: hexane/ethyl acetate=3/2)

Sources & evidence

ORD record
ord-9aeda1891f754190a23b6ed7b3aba932
Source dataset
uspto-grants-2014_07
Patent number
US08765739B2

Reaction notes

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