Sodium Carbonate → HCID 66937124, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 6-bromo-N-((4-fluorotetrahydro-2H-pyran-4-yl)methyl)pyridin-2-amine (1 g, 3.46 mmol), 5-chloro-2-fluoropyridin-4-ylboronic acid (1.092 g, 6.23 mmol), PdCl2(dppf)-CH2Cl2 adduct (0.282 g, 0.346 mmol) in DME (13 mL) and 2M aqueous Na2CO3 (5.19 mL, 10.38 mmol) in a sealed tube was heated at 100° C. for 2 hr. The mixture was cooled to ambient temperature and was diluted with EtOAc (˜50 mL) and saturated aqueous NaHCO3. The separated organic layer was washed with saturated aqueous NaHCO3 (2×), dried over Na2SO4, filtered off and concentrated in vacuo. The resulting residue was purified by column chromatography [SiO2, 80 g, EtOAc/heptane= 5/95 for 4 min, then EtOAc/heptane= 5/95 to 50/50 over 18 min, then EtOAc/heptane= 50/50]providing 5′-chloro-2′-fluoro-N-((4-fluorotetrahydro-2H-pyran-4-yl)methyl)-2,4′-bipyridin-6-amine as a colorless oil. Yield: 1.00 g. LCMS (m/z): 340.1 [M+H]+; Retention time=0.67 min.

Provenance & Evidence