Tributylvinyltin → HCID 21702077, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred mixture of N-(3-Bromo-pyridin-2-yl)-acetamide (1.20 g, 5.58 mmol) in anhydrous toluene (40 mL) under argon was added Tri-n-butyl(vinyl)tin (3.25 mL, 11.1 mmol) and Bis(triphenylphosphine)Palladium dichloride (0.40g, 0.57 mmol). This mixture was heated at 95° C. for 30 minutes and cooled to room temperature. This mixture was then diluted with saturated NaHCO3 solution (100 mL) and extracted with EtOAc (3×120 mL). The combined EtOAc extracts were dried (MgSO4), filtered and concentrated in vacuo. This was purified by a ISCO auto CombiFlash with a RediSep 35 g column, eluted with CH2Cl2-EtOAc, detected at 220 nM to give 420 mg of N-(3-Vinyl-pyridin-2-yl)-acetamide 78C in 46% yield.

Provenance & Evidence