2-(Tributylstannyl)pyridine → Tert-butyl 3-(3-(2,2'-bipyridin-5-yl)-7-(bis((2-(trimethylsilyl)ethoxy)methyl)amino)pyrazolo[1,5-a]pyrimidin-5-yl)-8-azabicyclo[3.2.1]octane-8-carboxylate

Participants

Reaction Steps

To tert-butyl 3-(7-(bis((2-(trimethylsilyl)ethoxy)methyl)amino)-3-(6-chloropyridin-3-yl)pyrazolo[1,5-a]pyrimidin-5-yl)-8-azabicyclo[3.2.1]octane-8-carboxylate (Int-2a) (2.66 mmol, 1904 mg) and Pd(PPh3)4 (0.27 mmol, 307 mg) in a 20 mL microwave vial was added 2-(Tributylstannyl)pyridine (5.25 mmol, 1.7 mL) and CH3CN (12 mL). The reaction was run in the microwave at 150° C. for 45 mins. The reaction was filtered through a pad of KF (˜7 g) and SiO2 (˜7 g) with the aid of EtOAc and fractions containing product were combined and concentrated to give a brown oil. Gradient column chromatography on silica (80 g) eluting with 5%-40% EtOAc/hexanes gave tert-butyl 3-(3-(2,2′-bipyridin-5-yl)-7-(bis((2-(trimethylsilyl)ethoxy)methyl)amino)pyrazolo[1,5-a]pyrimidin-5-yl)-8-azabicyclo[3.2.1]octane-8-carboxylate, LCMS tR=2.1 Min (5 min run, UV254nm). Mass calculated for, M+H 758.4, observed LC/MS m/z 758.3 (M+H).

Provenance & Evidence