Allyltributylstannane → HCID 19424398, compound

Participants

Reaction Conditions

Reaction Steps

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.

Provenance & Evidence