Cesium carbonate → 5-Methyl-2-(2H-1,2,3-triazol-2-yl)-N-[(1S,2S)-2-{[6-(trifluoromethyl)pyridin-3-yl]amino}cyclopentyl]benzamide

Participants

Reaction Conditions

Reaction Steps

N-[(1S,2S)-2-aminocyclopentyl]-5-methyl-2-(2H-1,2,3-triazol-2-yl)benzamide hydrochloride (Intermediate 7; 70 mg, 0.21 mmol), 5-bromo-2-(trifluoromethyl)pyridine (CAS number 436799-32-5; 73 mg, 0.32 mmol) and cesium carbonate (280 mg, 0.87 mmol) were suspended in toluene (3 ml). The reaction was degassed using nitrogen for 15 minutes. To this was then added BINAP (13 mg, 0.021 mmol) and tris(dibenzylideneacetone)dipalladium (0) (19 mg, 0.021 mmol) and the resulting reaction was heated to 100° C. overnight. The reaction mass was poured into water (20 ml) and the organics were extracted with ethyl acetate (3×20 ml). The combined organics were dried over sodium sulfate and concentrated in vacuo. This was then purified by reverse phase preparative HPLC (eluted with acetonitrile/water containing 0.1% ammonia) to afford the title compound.

Provenance & Evidence