Benzoyl Peroxide → N-(5-Bromo-thiazol-2-yl)-3-cyclohexyl-2-(1-oxo-1,3-dihydro-isoindol-2-yl)-propionamide

Participants

Reaction Conditions

Reaction Steps

To a suspension of (S)-3-cyclohexyl-2-(1-oxo-1,3-dihydro-isoindol-2-yl)-N-thiazol-2-yl-propionamide (Prepared in Example 1; 21 mg; 0.06 mmol) and N-bromosuccinimide (11 mg; 0.06 mmol) in anhydrous carbon tetrachloride (1.0 mL) was added benzoyl peroxide (1 mg; 0.004 mmol). The mixture was stirred at 95° C. in a sealed tube. After 1.5 h, N-bromosuccinimide (2 mg) and benzoyl peroxide (1 mg) were added and the mixture stirred for 30 min. further. The mixture was allowed to cool to room temperature and the solvent removed in vacuo. The residue was taken up into ethyl acetate and washed with water. The organic extract was washed with brine, dried over sodium sulfate, filtered and concentrated in vacuo. The crude residue was purified by flash chromatography (Biotage 12S, eluent: 20% ethyl acetate/hexanes to give 15 mg (58%) of N-(5-Bromo-thiazol-2-yl)-3-cyclohexyl-2-(1-oxo-1,3-dihydro-isoindol-2-yl)-propionamide as a grey foam: EI-HRMS m/e calcd for C20H23BrN3O2S (M+) 447.0616, found 447.0623.

Provenance & Evidence