P-Anisidine → HCID 68275989, compound

Participants

Reaction Conditions

Reaction Steps

In a sealed tube 4-methoxyaniline (18.34 mg, 0.149 mmol), tris(dibenzylideneacetone)dipalladium (4.55 mg, 4.97 μmol) and (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (5.75 mg, 9.93 μmol) were added to a suspension of (E)-2-bromo-N,N-diisopentyl-3-(3-(piperidin-1-yl)prop-1-en-1-yl)pyrazolo[1,5-a]pyridine-5-carboxamide (50 mg, 0.099 mmol) and potassium phosphate, dibasic (57.1 mg, 0.328 mmol) in toluene (5 ml). The mixture was heated at 110° C. overnight. The reaction mixture was cooled to room temperature, diluted with water and extracted with ethyl acetate (3×25 mL). The combined organics were washed with brine, dried over anh. sodium sulfate, filtered and concentrated. The residue was purified by SCX (silica-gel supported sulfonic acid) then by preparative HPLC (20% to 100% MeOH in water (0.05% TFA) in 7 minutes) to afford N,N-diisopentyl-2-((4-methoxyphenyl)amino)-3-(3-(piperidin-1-yl)prop-1-en-1-yl)pyrazolo[1,5-a]pyridine-5-carboxamide. LCMS m/z 546.4 (M+H)+ weak, 461.3 (strong); ret. time=2.19 min.

Provenance & Evidence