Allyltributylstannane → HCID 19424398, compound

HRID 743485Notes

Reaction equation

HRID 743485 reaction equation
Br[C:2]1[C:3]([C:8]([O:10][CH3:11])=[O:9])=[N:4][CH:5]=[CH:6][CH:7]=1.[CH2:12]([Sn](CCCC)(CCCC)CCCC)[CH:13]=[CH2:14]>CN(C=O)C>[CH2:14]([C:2]1[C:3]([C:8]([O:10][CH3:11])=[O:9])=[N:4][CH:5]=[CH:6][CH:7]=1)[CH:13]=[CH2:12]

Participants

4

Reactant 2

HCID 90628AllyltributylstannaneHCID 12828946Methyl 3-bromo-2-pyridinecarboxylate

Product 1

HCID 19424398HCID 19424398, compoundYield 111.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of methyl 3-bromo-pyridine-2-carboxylate (11.06 g; 51.2 mmol) Pd[PPh3 ]2Cl2 (1.09 g; 1.55 mmol), and allyl-tributyltin (20.34 g; 61.44 mmol) in DMF under nitrogen was heated at 90° C. for 9.5 hours and then stirred at room temperature overnight (17 hours) . The mixture was poured into ice/water (450 ml) and extracted with ether (4x) . The organic layer was washed with brine, dried over sodium sulfate, and concentrated in vacuo. The resulting residue (yellow oil) was purified by flash chromatography (20%-40% ethyl acetate in hexane) to afford 10.13 g of methyl 3-allyl-pyridine-2-carboxylate as an oil, which was converted into the corresponding HCl salt, m.p. 116°-119° C.

Workup

  1. extractionextracted with ether (4x)
  2. washThe organic layer was washed with brine
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe resulting residue (yellow oil) was purified by flash chromatography (20%-40% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-115efeb4c57540a1900addc4ae4eb75f
Source dataset
uspto-grants-1996_09
Patent number
US05556909

Reaction notes

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