Potassium Carbonate → (Cis)-2-[(5-bromopyridin-3-yl)amino]-N-(2,2,2-trifluoroethyl)cyclohexane carboxamide

Participants

Reaction Conditions

Reaction Steps

To a nitrogen degassed mixture of 3,5-dibromopyridine (8.5 g, 35.9 mmol), (cis)-2-amino-N-(2,2,2-trifluoroethyl)cyclohexanecarboxamide hydrochloride, I-5b, (9.35 g, 35.9 mmol), potassium carbonate (19.84 g, 144 mmol) and L-proline (0.826 g, 7.18 mmol), in DMSO (70 ml) was added copper(i) iodide (Strem® crushed) (0.683 g, 3.59 mmol). The reaction was sealed and heated at 80° C. for 64 hrs. Reaction was quenched into water (500 mL) and resulting solid product filtered and then slurry washed with water (50 mL). The wet solid was dissolved in ethyl acetate (400 mL), dried over sodium sulfate, filtered thru pad of silica to remove baseline material and filtrate concentrated to give 7.4 gm tan solid. Solid slurried in ˜50 mL diethyl ether for 15 min, filtered washed with hexane and solid sucked dry under nitrogen to give 5.73 gm product, I-5. LRMS (ESI) m/z 380.1 [(M+H)+; calcd for C14H17BrF3N3O: 380.1].

Provenance & Evidence