Cesium carbonate → rac-{1-[({7-[(3-Fluoropyridin-2-yl)methoxy]-2,5-dimethylpyrazolo[1,5-a]pyridin-3-yl}carbonyl)amino]-2-methylpentan-2-yl}carbamic Acid tert-butyl Ester

Participants

Reaction Steps

A solution of 49 mg (0.12 mmol) of rac-[1-{[7-hydroxy-2,5-dimethylpyrazolo[1,5-a]pyridine-3-carbonyl)amino]}-1-methylbutyl)carbamic acid tert-butyl ester (Example 141A) in 2.1 ml of DMF was admixed with 78 mg (0.24 mmol) of caesium carbonate and 69 mg (0.360 mmol) of 2-bromomethyl-3-fluoropyridine (Example 143A). The reaction mixture was stirred at room temperature for 18 hours. The solvent was evaporated off under reduced pressure and the residue was partitioned between dichloromethane and water. The organic phase was removed and concentrated under reduced pressure. The residue was purified by preparative HPLC chromatography (Method 21), which gave 21 mg (33% yield, 96% pure) of the target compound.

Provenance & Evidence