1,2-Dimethoxyethane → HCID 86700859, compound

Participants

Reaction Conditions

Reaction Steps

A vial was charged with methyl 2-(1-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-2-oxabicyclo[2.2.2]octan-4-yl)acetate (20 mg, 0.052 mmol), N-(4-bromophenyl)-5-cyclobutyl-1,3,4-oxadiazol-2-amine (30.5 mg, 0.104 mmol), PdCl2(dppf)-CH2Cl2adduct (6.34 mg, 7.77 μmol), potassium phosphate (21.98 mg, 0.104 mmol), dimethoxyethane (0.6 ml), methanol (0.2 ml), and water (0.1 ml) at room temperature. The vial was sealed, flushed with nitrogen for three times and heated at 80° C. for 16 hours. The mixture was purified by flash chromatography (heptanes/acetone 1/1, washed with acetone/ethanol 1/1) to afford methyl 2-(1-(4′-((5-cyclobutyl-1,3,4-oxadiazol-2-yl)amino)-[1,1′-biphenyl]-4-yl)-2-oxabicyclo[2.2.2]octan-4-yl)acetate (40 mg, 40% purity, 65% yield) as white solid. LC/MS, ESI-MS(+1) m/z 474.19, RT 1.41 (Condition E).

Provenance & Evidence