Sodium Carbonate → HCID 9969257, compound

Participants

Reaction Steps

[2-(4-Bromophenoxy)propyl][(methylethyl)sulfonyl]amine (300 mg, 0.892 mmol, prepared in example 1), 3-chlorobenzeneboronic acid (170 mg, 1.09 mmol), dichlorobis(triphenylphosphine)palladium(II) (25 mg, 0.036 mmol), 2 M sodium carbonate (320 mg in 1.5 mL water) and 1,2-dimethoxyethane (6.0 mL) were combined in a 15 ml round bottom flask, fitted with a condenser, stirbar, and in a temperature regulated oil bath, and heated at reflux 85 C. in a nitrogen system overnight. The reaction mixture was quenched with water and extracted three times with 25 mL of methylene chloride. The organic extracts were combined, dried over anyhydrous magnesium sulfate, filtered, and concentrated under reduced pressure, yielding 190 mg brown viscous oil. This material was purified via silica gel chromatography, utilizing a Chromatotron® with a 2000 μm rotor in a 1:1 hexane:ethyl acetate solvent system, yielding the title compound (175 mg, 53%) as a yellow foam. Electrospray-MS 369.0 (M*+1).

Provenance & Evidence