Benzoyl Peroxide → (E)-N-(5-bromo-thiazol-2-yl)-3-cycloheptyl-2-(4-methanesulfonyl-phenyl)-acrylamide

Participants

Reaction Conditions

Reaction Steps

A suspension of (E)-3-cycloheptyl-2-(4-methanesulfonyl-phenyl)-N-thiazol-2-yl-acrylamide (prepared in Example 5, 202 mg, 0.5 mmol) and N-bromosuccinimide (89 mg, 0.5 mmol) in carbon tetrachloride (2 mL) at 25° C. was treated with benzoyl peroxide (6 mg, 0.025 mmol). The resulting reaction mixture was heated to 90° C. where it was stirred overnight at this temperature. The reaction mixture was allowed to cool to 25° C. and then concentrated in vacuo. The residue was dissolved in ethyl acetate (25 mL). The organic phase was then washed with water (1×30 mL) and a saturated aqueous sodium chloride solution (1×30 mL), dried over anhydrous magnesium sulfate, filtered, and concentrated in vacuo. Biotage chromatography (FLASH 40M, Silica, 4/1 hexanes/ethyl acetate) afforded the (E)-N-(5-bromo-thiazol-2-yl)-3-cycloheptyl-2-(4-methanesulfonyl-phenyl)-acrylamide (86 mg, 36%) as a white solid: mp 159-163° C.

Provenance & Evidence