Benzo(B)Thiophene-2-Boronic Acid → 2-(1-Benzothien-2-yl)-5-[(2-phenylbutanoyl)amino]benzamide

Participants

Reaction Steps

A solution of 500 mg (1.23 mmol) of the compound of Example 5A, 262 mg (1.47 mmol) of 1-benzothien-2-ylboronic acid, 1.34 ml (2.70 mmol, 2M solution in water) of sodium carbonate and 42 mg (0.061 mmol) of bis(triphenylphosphine)palladium(II) chloride in 10 ml of dimethoxyethane are stirred under reflux for 3 hours. The solution is cooled to room temperature and then partitioned between 500 ml of ethyl acetate and water, and the aqueous phase is extracted twice with 200 ml of ethyl acetate. The combined organic phases are washed with saturated sodium chloride solution, dried over magnesium sulfate, filtered with suction and concentrated. The residue is dissolved in dimethyl sulfoxide and purified by preparative RP-HPLC with acetonitrile and water. 146 mg (29% of theory) of the title compound are obtained.

Provenance & Evidence