Sodium Carbonate → (3R,4S)-4-[4-(2-Methoxypyridin-3-yl)phenoxy]-1-pyridin-3-yl-pentan-3-ol

Participants

Reaction Steps

Prepared according to the method described in Example 21b) from 2M aqueous sodium carbonate (2.0 ml), (1S,2R)-4-(2-hydroxy-1-methyl-4-pyridin-3-ylbutoxy)benzeneboronic acid (Example 21a), 0.508 g), 3-iodo-2-methoxypyridine (0.730 g, J. Org. Chem., 1988 53(12), 2740), and tetrakis(triphenylphosphine)palladium(0) (0.216 g) in ethanol (10 ml). The mixture was heated at reflux for 6 hours. After cooling to room temperature the mixture was concentrated under reduced pressure. The residue was purified by column chromatography over silica eluting with ethyl acetate to give an oil, which was further purified by normal phase HPLC eluting with 2-propanol:dichloromethane (3:97) to give the title compound as an oil.

Provenance & Evidence