Potassium Phosphate, Tribasic → HCID 59565188, compound

Participants

Reaction Conditions

Reaction Steps

A suspension of 8-chloro-imidazo[1,5-a]pyridine-7-carboxylic acid methyl ester (500 mg, 2.38 mmol), 4-bromo-2-fluoroaniline (543 mg, 2.86 mmol), Pd2dba3 (110 mg, 0.12 mmol), 2-dicyclohexylFphosphino-2′,6′-diisopropoxybiphenyl (224 mg, 0.48 mmol) and K3PO4 (710 mg, 3.33 mmol) in toluene (10 mL) was degassed and then heated at 100° C. for 18 hours. The reaction mixture was then cooled to room temperature, diluted with ethyl acetate and filtered. The filtrate was washed with water and brine, then loaded onto a 10 g Isolute® SCX-2 cartridge which was eluted with methanol and then a 2M solution of ammonia in methanol. The appropriate fractions were combined and concentrated in vacuo. The resultant residue was subjected to flash chromatography (Si-PPC, gradient 0% to 20%, ethyl actetate in DCM) to afford the title compound as a yellow oil (240 mg, 28%). LCMS (method B): RT=3.40 min, [M+H]+=364/366.

Provenance & Evidence