Benzoyl Peroxide → HCID 10115151, compound

Participants

Reaction Conditions

Reaction Steps

A suspension of (E)-3-cyclopentyl-2-(4-methanesulfonyl-phenyl)-N-thiazol-2-yl-acrylamide (prepared in Example 3, 0.44 g, 1.17 mmol) and N-bromosuccinimide (0.20 g, 1.17 mmol) in carbon tetrachloride (4 mL) at 25° C. was treated with benzoyl peroxide (14.17 mg, 0.058 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 (50 mL). The organic phase was then washed with water (1×50 mL) and a saturated aqueous sodium chloride solution (1×50 mL), dried over anhydrous magnesium sulfate, filtered, and concentrated in vacuo. Biotage chromatography (FLASH 40M, Silica, 4/1 to 1/1 hexanes/ethyl acetate) afforded (E)-N-(5-bromo-thiazol-2-yl)-3-cyclopentyl-2-(4-methanesulfonyl-phenyl)-acrylamide (115 mg, 22%) as white solid: mp 202-205° C.

Provenance & Evidence