Sodium Carbonate → 6-((S)-2-Amino-3-phenylpropylamino)-3-(3-methylphenyl)-2-(4-pyridyl)pyridine

Participants

Reaction Steps

To a stirred, degassed mixture of 6-((S)-2-Amino-3-phenylpropylamino)-3-bromo-2-(4-pyridyl)pyridine (4.2 gm, 10.9 mmole), 3-methylbenzene boronic acid (1.8 gm, 13 mmole), in aqueous 2 M Na2CO3 (50 mL) and toluene (50 mL) at rt was added Pd(PPh3)4(400 mg, 0.35 mmole). The mixture was heated to reflux for 12 hrs, cooled to rt, and extracted with toluene. The combined organic layers were washed with brine, concentrated and purified (SiO2, CH2Cl2/MeOH/NH4OH: 100/11/8) to give the title compound. MS (m/z): Calcd. C26H26N4 (M+): 394, found (M+H)+: 395.1.

Provenance & Evidence