Sodium Carbonate → N-Methyl-4-phenyl-3-pyridinamine

Participants

Reaction Conditions

Reaction Steps

To a solution of (4-iodo-pyridin-3-yl)-methyl-amine (225 mg, 0.96 mmol, example 36, intermediate b) in DME (5 mL) were added phenyl boronic acid (234 mg, 1.92 mmol) and 2M aqueous Na2CO3 solution (2 mL) and the reaction mixture was purged with nitrogen for 15 min. Then Pd(OAc)2 (22 mg, 0.1 mmol) and triphenylphosphine (50 mg, 0.19 mmol) were added and the reaction mixture was stirred at 100° C. for 5 hours. The reaction mixture was poured on 30 mL 10% aqueous NaHCO3 solution and 30 mL EtOAc and the layers were separated. The aqueous layer was extracted with 30 mL EtOAc. The combined organic layer was washed with brine (30 mL), dried over Na2SO4 and evaporated. The residue was purified by column chromatography eluting with a gradient of n-hexane:EtOAc (80:20 to 70:30) to yield the desired compound as a yellow solid (160 mg, 90%) MS (ESI): m/z=185.0 [M+H]+.

Provenance & Evidence