Sodium Carbonate → HCID 66936987, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 6-bromo-N-((4-methyltetrahydro-2H-pyran-4-yl)methyl)pyridin-2-amine (750 mg, 2.63 mmol), 5-chloro-2-fluoropyridin-4-ylboronic acid (830 mg, 4.73 mmol), PdCl2(dppf)-CH2Cl2 Adduct (215 mg, 0.263 mmol) in DME (12 mL) and 2M aqueous Na2CO3 (4 mL, 8.00 mmol) in a sealed tube was heated at 103° C. for 4 hr. The mixture was allowed to cool to ambient temperature and was diluted with EtOAc (˜50 mL) and saturated aqueous NaHCO3 solution. The separated organic layer was washed with saturated aqueous NaHCO3 solution (2×), dried over Na2SO4, filtered off and concentrated in vacuo. The resulting residue was purified by column chromatography [SiO2, 40 g, 20 min, EtOAc/heptane= 0/100 for 2 min, then EtOAc/heptane= 5/95 to 50/50 over 18 min, then EtOAc/heptane= 50/50] providing 5′-chloro-2′-fluoro-N-((4-methyltetrahydro-2H-pyran-4-yl)methyl)-2,4′-bipyridin-6-amine as a colorless oil. Yield: 691 mg. LCMS (m/z): 336.2 [M+H]+; Retention time=0.66 min.

Provenance & Evidence