Sodium Carbonate → 5-(2-(4-Fluorophenyl)oxazol-4-yl)-3-methoxypyridin-2-amine

Participants

Reaction Steps

A mixture of 3-methoxy-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-amine (200 mg, 0.8 mmol) and 2-(4-fluorophenyl)oxazol-4-yl trifluoromethanesulfonate (250 mg, 0.8 mmol), and 2.0 M aqueous Na2CO3 (1.2 mL, 2.4 mmol) in DME (2.0 mL) was sparged with Ar. Dichlorobis(triphenylphosphine)palladium(0) (281 mg, 0.4 mmol) was added and the reaction mixture was irradiated at 150° C. for 15 min in a microwave reactor. After cooling to rt, the reaction mixture was diluted with water and extracted with EtOAc (3×). The combined organic layers were dried over sodium sulfate, filtered and concentrated in vacuo. The residue was purified by flash chromatography over (SiO2, 100:0-0:100 hexanes-EtOAc) to provide 145 mg of 5-(2-(4-fluorophenyl)oxazol-4-yl)-3-methoxypyridin-2-amine: LCMS (m/z): 286.1 (MH+), tR=0.68 min.

Provenance & Evidence