Sodium Carbonate → 2-(4'-Methanesulfinyl-biphenyl-4-yl)-5-methyl-4-(2-pyrrolidin-1-yl-ethyl)-oxazole

Participants

Reaction Steps

To a stirred solution of 2-(4-Bromo-phenyl)-5-methyl-4-(2-pyrrolidin-1-yl-ethyl)-oxazole (50 mg, 0.149 mmol), sodium carbonate (47.5 mg, 0.448 mmol) and 4-Methylsulfinylbenzene boronic acid (137.3 mg, 0.75 mmol) in toluene (2.5 mL), water (0.75 mL) and ethanol (1 mL) under nitrogen was added Tetrakis(triphenylphosphine) palladium (0) (17. 2 mg, 0.015 mmol). The reaction was then heated to reflux for 48 h. The reaction was allowed to cool and bound to a SCX-2 cartridge (5 g). The cartridge was washed with one cartridge volume of dimethylformamide and two volumes of methanol. The product was eluted using 2M ammonia in methanol. The ammonia/methanol solution was evaporated on a Genevac® HT4. The sample was further purified by prep-LCMS. The resulting acetonitrile/water fractions were combined and evaporated using a Genevac® HT4 to give 17.8 mg of a colourless oil (30%). MS (m/e): 395.2 (M+1)

Provenance & Evidence