Ammonium Chloride → HCID 67528783, compound

Participants

Reaction Conditions

Reaction Steps

N-(5-chloro[1,2,4]triazolo[1,5-a]pyridin-2-yl)nicotinamide ((B4), 141.00 mg; 0.52 mmol; 1.00 eq.), 2,2-dimethylethenylboronic acid (Synthonix, 102.96 mg; 1.03 mmol; 2.00 eq.), cesium fluoride (156.53 mg; 1.03 mmol; 2.00 eq.) and bis(triphenylphosphine)palladium(II) chloride (36.16 mg; 0.05 mmol; 0.10 eq.) were flushed with nitrogen in a sealed vial. THF (degassed with nitrogen, 1.50 mL) and water (1 mL) were then added and the mixture was heated at 120° C., O/N in an oil bath. A solution of saturated NH4Cl was added and the reaction mixture was extracted with EtOAc (twice). Combined Organic phases were washed with brine, dried over magnesium sulfate, filtered and concentrated to give 186 mg of a yellow foam. Hydrochloride salt was then obtained by addition of Et2O/HCl (1 M solution) to a solution of this crude in DCM. The precipitate obtained was filtered and dried under vacuum at 40° C. to give the title compound as a beige solid (181 mg, 96%). HPLC, Rt: 2.05 min. (purity 92.3%). LC/MS, M+(ESI): 293.9, M−(ESI): 291.9.

Provenance & Evidence