Triethylamine → HCID 69588931, compound

Participants

Reaction Steps

In a sealed pressure tube under a nitrogen atmosphere, 3-bromopyridine (264.67 mg, 1.675 mmol), (2S)-N-tert-butoxycarbonyl-2-vinylpyrrolidine (300 mg, 1.52 mmol), tri-o-tolylphosphine (46.82 mg, 0.153 mmol), palladium(II) acetate (34.53 mg, 0.15 mmol), triethylamine (2 mL) and acetonitrile (20 mL) were stirred at 90° C. for 14 h. The tube was cooled and the contents were slowly poured into a stirred saturated aqueous NaHCO3 solution (20 mL) and extracted with chloroform (4×20 mL). The combined chloroform extracts were dried (K2CO3), filtered and concentrated under vacuum to give 500 mg of a viscous dark oil, which was chromatographed with an ethyl acetate:hexane gradient (1:4 to 1:1, v/v) as eluant. Selected fractions containing the product were combined and concentrated on a rotary evaporator to give 310 mg (84.0% yield) of pale-yellow oil.

Provenance & Evidence