Hydrochloric Acid → [3-Hydroxy-5-(1H-indol-4-YL)-phenyl]-(6-hydroxymethyl-pyridin-3-YL)-methanone

Participants

Reaction Conditions

Reaction Steps

[3-Bromo-5-(4-methoxy-benzyloxy)-phenyl]-(6-methyl-pyridin-3-yl)-methanone. A 1.6 M solution of n-BuLi in hexane (1.8 mmol) was added dropwise to a stirred mixture of 1,3-dibromo-5-(4-methoxy-benzyloxy)-benzene (600 mg, 1.6 mmol) in dry ether (6 mL) at −78° C. The resulting solution was stirred at −78° C. for 30 min, and then 6-methyl-nicotinonitrile (190 mg, 1.6 mmol) in dry ether (4 mL) was added dropwise. The mixture was stirred at −78° C. for 1 h, and then the temperature was allowed to rise to 0° C. 2N HCl was added with stirring. The aqueous was then basified with 1N NaOH solution and extracted with methylene chloride three times. The combined organic phase was washed with brine, dried, and concentrated to afford the crude product which was further purified by flash chromatography (3:1 hexane/EtOAc) to yield the desired product as a yellow oil (600 mg, 90%).

Provenance & Evidence