Toluene → HCID 21830703, compound

Participants

Reaction Conditions

Reaction Steps

Prepared according to the method described in Example 33a) from toluene (3 ml), aqueous sodium carbonate (2 M, 1.4 ml), (±)-1-(4-bromophenoxy)-4-(3-pyridyl)-2-butanol (0.51 g), ethanol (0.8 ml), 2,4-dichlorobenzeneboronic acid (0.32 g) and tetrakis(triphenylphosphine)palladium(0) (75 mg) with heating at 120° C. for 4 hours. The residue obtained after work up was purified by column chromatography over silica eluting with dichloromethane then ether then ethyl acetate to give (±)-1-(2',4'-dichlorobiphenyl-4-yloxy)-4-(3-pyridyl)-2-butanol (0.48 g). A sample that had been purified by reverse phase HPLC was converted to the oxalate salt by treatment of the parent compound in ether with a saturated ethereal solution of oxalic acid. The precipitated salt was filtered to give the title compound (0.23 g).

Provenance & Evidence