Sodium Carbonate → (1S,2R)-4'-(2-Hydroxy-1-isopropyl-4-pyridin-3-yl-butoxy)biphenyl-3-carbonitrile

Participants

Reaction Conditions

Reaction Steps

Prepared according to the method described in Example 12b) from 3-cyanobenzeneboronic acid (0.40 g), (3S,4R)-3-(4-bromophenyloxy)-2-methyl-6-(3-pyridyl)hexan-4-ol (0.90 g, Example 61d)), 2M aqueous sodium carbonate (2.72 ml) and tetrakis(triphenylphosphine)palladium(0) (0.160 g) in ethanol (4 ml). The reaction mixture was heated at 90° C. for 4 hours. After cooling, the solution was poured onto water, and extracted with ethyl acetate. The combined extracts were washed with brine, dried over magnesium sulfate, and filtered. The filtrate was concentrated under reduced pressure, dissolved in dichloromethane, filtered and purified by normal-phase HPLC eluting with a gradient of 0-25% ethanol in dichloromethane to give the title compound as a gum (0.54 g).

Provenance & Evidence