1,2-Dimethoxyethane → Methyl 4-(2-aminopyridin-3-yl)-2-fluorobenzoate

Participants

Reaction Conditions

Reaction Steps

To 3-bromopyridin-2-amine (5 g, 28.9 mmol) in 500 mL round bottom flask was added (3-fluoro-4-(methoxycarbonyl)phenyl)boronic acid (7.44 g, 37.6 mmol), PdCl2(dppf)-DCM (2.115 g, 2.89 mmol), DME (108 mL) and 2M Na2CO3 solution (36.1 mL). The reaction mixture was heated in an oil bath at 110° C. for 4 h. The reaction mixture was diluted with EtOAc and washed with water three times, dried over Na2SO4, filtered and concentrated. The crude product was purified by flash chromatography eluting with 0-100% of EtOAc (containing 10% of MeOH)/heptane yielding 5.6 g of methyl 4-(2-aminopyridin-3-yl)-2-fluorobenzoate in 79% yield. LCMS (m/z): 247.1 (MH+), 0.50 min.

Provenance & Evidence