Pivalic acid → HCID 178451149, compound

Participants

Reaction Steps

To a vial were added 2,6-dibromo-4-methylpyridine (121 mg, 0.482 mmol), cis-butyl 4-[1-hydroxy-1-(1,3-thiazol-2-yl)ethyl]cyclohexanecarboxylate (75 mg, 0.241 mmol), potassium carbonate (100 mg, 0.722 mmol), pivalic acid (5.59 μl, 0.048 mmol), tetrakis(triphenylphosphine)palladium(0) (11.1 mg, 9.63 μmol) and N,N-dimethylacetamide (760 μl). The vial was sealed and placed under argon through 3 cycles of evacuation and argon flushing then reacted at 80° C. overnight. The resulting mixture was cooled, diluted with ethyl acetate, filtered through a plug of CELITE and concentrated. The residue was purified by column chromatography on silica gel (0-100% ethyl acetate/hexanes) to afford racemic-cis-butyl 4-{1-[5-(6-bromo-4-methylpyridin-2-yl)-1,3-thiazol-2-yl]-1-hydroxyethyl}-cyclohexanecarboxylate.

Provenance & Evidence