Potassium Carbonate → HCID 89487095, compound

Participants

Reaction Conditions

Reaction Steps

In a microwave vial equipped with a magnetic stirrer, 3,5-Dibromopyridine (Aldrich Chemical) (1 g, 4.22 mmol), (R)-2-amino-N-(2,2,2-trifluoroethyl)propanamide hydrochloride (0.872 g, 4.22 mmol), Potassium carbonate (2.334 g, 16.89 mmol) were added followed by DMSO (6.03 ml, 0.7M). The reaction mixture was stirred and purged under nitrogen for 10 minutes, then Copper (I) Iodide (0.08 g, 0.422 mmol) was added and the reaction mixture was heated in an oil bath at 120° C. for 2 hours. The cooled reaction mixture was then partitioned between Isopropanol (IPA): Chloroform (1:3) and Water, the aqueous layer was extracted with twice with IPA:Chloroform mixture. The combined organic layers were extracted with water, dried over anhydrous magnesium sulfate, filtered and concentrated to give the crude sample. Purification on silica (100 g SNAP Biotage column) using 0-5% Methanol/Dichloromethane gave (R)-2-(5-bromopyridin-3-ylamino)-N-(2,2,2-trifluoroethyl)propanamide, I-1, (1.03 g, 74.8% yield) LRMS (ESI) m/z 325.9 [(M+H)+; calcd for C10H11BrF3N3O: 326.01]

Provenance & Evidence