Cesium carbonate → N-(4-(3,4'-bipyridin-2-yloxy)phenyl)benzo[d]thiazol-2-amine

Participants

Reaction Steps

A 25 ml round bottomed flask was charged with 4-(3-(pyridin-4-yl)pyridin-2-yloxy)benzenamine (0.1531 g, 0.58 mmol), 2-bromobenzo[d]thiazole (0.1874 g, 0.88 mmol), Palladium acetate (0.0264 g, 0.12 mmol), 2-(dicyclohexylphosphino)biphenyl (0.0878 g, 0.23 mmol), and cesium carbonate (0.077 ml, 0.81 mmol) in toluene/t-BuOH (5/1) at 100° C. overnight. Upon completion, the reaction was allowed to cool to room temperature. The crude product was adsorbed onto a plug of silica gel and chromatographed through a Biotage pre-packed silica gel column (25M), eluting with a gradient of 1% to 5% MeOH in DCM. Further purification was performed by reverse-phase preparative HPLC using a Phenomenex Gemini column, 5 micron, 150×30 mm, 0.1% TFA in ACN/H2O, gradient 10% to 100% over 15 min. The product peak fractions were collected and organic solvents were removed. The aqueous solution was diluted with water (5 mL) and sodium bicarbonate was added until the pH˜10. The solution was extracted with DCM. The organic extract was washed with water, brine, dried with magnesium sulfate, filtered, and concentrated to provide N-(4-(3,4′-bipyridin-2-yloxy)phenyl)benzo[d]thiazol-2-amine. MS (ESI, pos. ion) m/z: 397.0 (M+1). IC50 (uM) +++++.

Provenance & Evidence