Sodium Bicarbonate → HCID 136166894, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of (E)-3-(4-bromo-phenyl)-3-phenyl-1-pyridin-4-yl-propan-1-one oxime (example 5, 100 mg) in toluene (0.9 mL) and water (0.1 mL) was added potassium cyclopropyltrifluoroborate (47 mg), tri-potassium phosphate monohydrate (199 mg) and tetrakis(triphenylphosphine) palladium (0) (6 mg). The mixture was heated to 100° C. overnight. After cooling to rt a saturated aqueous solution of NaHCO3 was added, the phases were separated and the inorganic one was extracted with EtOAc (2×). The combined organic layers were washed with brine, dried over Na2SO4, filtered and concentrated in vacuo. The crude product was purified by flash chromatography on silica gel (EtOAc/n-heptane 1:1) to yield (E)-3-(4-cyclopropyl-phenyl)-3-phenyl-1-pyridin-4-yl-propan-1-one oxime (43 mg, 49%) as a white foam, MS (ESI+): m/z=343.3 ([M+H]+).

Provenance & Evidence