4-Vinylpyridine → 6-chloro-5-[(E)-2-pyridin-4-ylvinyl]pyridin-3-amine

Participants

Reaction Steps

A solution of 3-amino-5-bromo-6-chloropyridine (2.0 g, 9.64 mmol), Pd2(dba)3 (440 mg, 0.48 mmol), tri-o-tolylphosphine (438 mg, 1.44 mmol), 4-vinylpyridine (2.08 mL, 19.28 mmol), and triethylamine (4.03 mL, 29 mmol) in DMF (30 mL) was stirred at 100° C. for 15 hours, cooled to room temperature, treated with ethyl acetate (200 mL), washed twice with brine, dried (MgSO4), filtered and concentrated. The residual solid recrystallized from hexanes/dichloromethane to provide desired product (1.86 g, 84%). MS (APCI) m/e 232 (M+H)+.

Provenance & Evidence