2,3-Butanediol → HCID 9968749, compound

Participants

Reaction Conditions

Reaction Steps

4-Cyanobenzeneboronic acid (171 mg, 1.16 mmol, prepared in example 25), tetrakis(triphenylphosphine)palladium(0) (69 mg, 0.063 mmol), 2 M sodium carbonate (1.6 mL), and [(2R)-2-(4-bromophenoxy)propyl][(methylethyl)sulfonyl]amine (310 mg, 0.922 mmol) were combined in a 15 mL round bottomed flask with dimethylethylene glycol (6.15 mL, DME), fitted with a condenser, stirbar, and in a temperature regulated oil bath, and refluxed in a nitrogen system to 85° C., overnight. The reaction was allowed to cool to room temperature, and quenched with 15 mL of water, and extracted three times with 15 mL ethyl acetate. The organic layer was dried with magnesium sulfate, filtered through Celite®, and concentrated under reduced pressure, yielding 470 mg viscous black oil. This material was further purified using a 4000 uM rotor on a Chromatotron® in a 1:1 hexanes:ethyl acetate solvent system yielding the final title compound (57.5 mg, 18%) as white crystals.

Provenance & Evidence