Ammonium Chloride → HCID 136166849, compound

Participants

Reaction Conditions

Reaction Steps

To a suspension of tris(dibenzylideneacetone)dipalladium (23 mg), sodium tert-butylate (83 mg), 2(di-tertbutylphosphino)biphenyl (15 mg) and 3-(4-bromo-phenyl)-1-pyridin-4-yl-3-o-tolyl-propan-1-one oxime (example 31, 200 mg) in toluene (10 mL) was added a solution of N (2-methoxyethyl)methylamine (158 mg) in toluene (10 mL). The reaction mixture was stirred at 80° C. overnight, cooled to room temperature and a saturated aqueous solution of NH4Cl was added. The phases were separated and the inorganic layer was extracted with EtOAc (2×). The combined organic layers were washed with brine, dried over Na2SO4, filtered and concentrated in vacuo. Column chromatography on silica gel (EtOAc/n-heptane 2:1 to EtOAc) yielded (E)-3-{4-[(2-methoxy-ethyl)-methyl-amino]-phenyl}-1-pyridin-4-yl-3-o-tolyl-propan-1-one oxime containing less than 10% of the Z isomer (88 mg, 43%) as a yellow foam, MS (ESI+): m/z=404.3 ([M+H]+).

Provenance & Evidence